Your question could be about retirement. Or maybe it's about a property, taxes, investments, insurance or family. It could also be the most important question is one you didn't know to ask.
Because your financial life is interconnected, the answer to one question can change what makes sense somewhere else.
In our experience especially true when investment real estate is part of your financial life. A decision that looks good at the property level can look very different when its impact on cash flow, taxes, retirement, investments and your other goals is considered.
Explore some of the questions we help clients answer.
Retirement & Financial Independence
Can I retire? How soon? How much can I spend?
We believe retirement planning is about more than reaching a certain age or portfolio balance. We seek to help clients evaluate when they can retire, how much they can comfortably spend, where retirement income will come from, and how decisions involving investments, real estate, taxes, Social Security and longevity can affect the plan.
Explore Retirement Questions
Do I have enough to retire?
How soon can I retire?
Can I retire earlier than I think?
How much can I comfortably spend in retirement?
What happens if I work another year or two?
Could I work part-time instead of continuing full-time?
What happens if one spouse retires before the other?
What is the right age for me to retire?
How much should I be saving during my remaining working years?
Where will my retirement income come from?
Which accounts should I spend from first?
How much should I keep in cash during retirement?
How will inflation affect my retirement?
What happens if investment returns are worse than expected?
What happens if one of us lives much longer than expected?
What could derail an otherwise successful retirement plan?
Am I saving too much for retirement at the expense of enjoying life today?
What would have to change for me to retire sooner?
Is my real estate helping me get where I want to go?
We have seen that owning investment real estate can build substantial wealth, but property value and gross rent don't tell the whole story. The more important questions are how the property is actually performing, what it's contributing to your financial life, and whether the equity could be working harder somewhere else.
That's why I developed The Real Estate Income Lab®. It combines real estate conversation and coaching, deeper property-level financial analysis, and integration into your financial plan. We work beneath the surface numbers to better understand cash flow, expenses, NOI, cap rate, return on equity, debt and risk, and then model what keeping, improving, refinancing, exchanging, selling or repositioning a property could mean for your broader financial life.
One of the things this process can uncover is what I call The 5% Real Estate Performance Gap®, the potential difference between what an owner believes a property is producing and what deeper analysis reveals after accounting for expenses, vacancy, repairs, capital improvements, debt and other factors that may be overlooked.
The point isn't simply to grade the property. It's to understand what the real estate is doing for you, and what your alternatives could do instead.
Explore Real Estate Questions
Is my rental property actually a good investment?
How do I know how well my rental property is performing?
Is the cash flow I think I'm receiving the cash flow the property is actually producing?
What expenses or assumptions might I be overlooking when I calculate my real estate returns?
What is the real return I'm earning on my equity?
Is appreciation disguising poor investment performance?
Should I keep, improve, refinance, exchange or sell a property?
Is too much of my net worth tied up in real estate?
How much of my investments should be in real estate?
Could the equity in one of my properties work harder somewhere else?
What would happen to my overall financial plan if I invested my real estate equity differently?
How do I compare a rental property with stocks, bonds or other investments?
What return should I expect for the additional risk and work of owning real estate?
Is my short-term rental producing enough additional return to justify the additional work?
Would my short-term rental perform better as a long-term rental?
Am I properly accounting for vacancy, repairs, capital expenditures and management?
Should I pay off the mortgage on a rental property?
Is a very low mortgage rate a good reason to keep a property?
Should I use leverage to buy another property?
Should I sell a property before I retire?
Should I keep rental properties during retirement for income?
How will selling a property affect my taxes?
How much depreciation recapture could I owe?
Should I do a 1031 exchange?
What happens if I don't want another directly owned rental after a 1031 exchange?
Should I consider a Delaware Statutory Trust (DST)?
Could a 1031-to-721 strategy make sense?
Should I own real estate in an LLC or another entity?
How should my real estate be handled in my estate plan?
Am I keeping this property because it's a good investment, or simply because I've owned it for a long time?
Why do we earn a good income but still feel financially constrained?
Cash flow connects what you earn and own with the life you actually want to live. We help clients understand where their money is going, how real estate contributes to or draws from cash flow, how much liquidity they need, and whether debt, spending and savings decisions are supporting their broader goals.
Explore Cash Flow & Debt Questions
Why do we earn a good income but still feel cash-flow constrained?
Where is our money actually going?
How much should we reasonably be spending?
How much cash should we keep available?
Are our emergency reserves adequate?
Should we pay off our mortgage before retirement?
Should I pay off a HELOC or invest the money instead?
Which debt should I pay off first?
Is inexpensive debt worth keeping?
Should I borrow or pay cash for a major purchase?
Can we afford another home or major purchase without hurting the rest of the plan?
Are we helping our adult children more than we can afford?
How do we turn a high income and substantial net worth into more financial flexibility?
Investments
Are my investments taking the right risks for what I'm trying to accomplish?
An investment portfolio shouldn't be considered separately from the rest of your financial life. We help clients evaluate allocation, diversification, risk, costs, taxes and account structure while considering how their investments work alongside real estate, retirement income and other resources.
Explore Investment Questions
Is my investment allocation right for me?
Am I taking too much risk?
Am I taking too little risk?
Should I become more conservative as I get older?
Does becoming older automatically mean I should own fewer stocks?
Are my investments properly diversified?
How much international investment exposure should I have?
Am I paying too much for my investments?
Do I own too many accounts or investments?
Should I consolidate accounts?
Where should different investments be held for tax efficiency?
What should I do with a concentrated stock position?
Should I own REITs if I already own directly held real estate?
Should alternative investments be part of my plan?
Does an annuity make sense for me?
How should my investment strategy change once I retire?
How should my real estate and investment portfolio be considered together?
Is my investment portfolio designed around my financial plan, or is my financial plan being forced to accommodate my investments?
Taxes
Am I making tax decisions based on what's best for my goals, preferences and lifestyle?
We have seen cases when paying less tax this year isn't always the same as achieving a better long-term outcome. We help clients evaluate tax decisions across multiple years, including retirement contributions, Roth conversions, withdrawals, real estate sales, 1031 exchanges, Social Security and Medicare, within the context of the overall financial plan.
Explore Tax Questions
How can I reduce my taxes?
More importantly, how can I reduce my lifetime taxes?
Should I contribute to a traditional or Roth retirement account?
Should I do a Roth conversion?
How much should I convert?
Could a Roth conversion actually make my financial plan worse?
Should I convert now or wait?
What happens when Required Minimum Distributions begin?
How can I manage my tax brackets over multiple years?
Which accounts should I withdraw from first in retirement?
How will Social Security affect my taxes?
Could my income increase my Medicare premiums?
What happens tax-wise if I sell a rental property?
How much depreciation recapture might I owe?
Can I defer taxes through a 1031 exchange?
How should an inheritance affect my tax planning?
How can charitable giving be incorporated into my tax plan?
Am I making decisions to minimize this year's tax bill, or to improve my lifetime financial outcome?
Insurance & Risk
Which risks could do the most damage to my financial future, and what's the best way to address them?
A strong financial plan should consider what happens when life doesn't go according to plan. We help clients evaluate the financial impact of death, disability, long-term care, liability and other risks; determine which risks they can afford to absorb; and consider how insurance, financial resources and real estate income may help mitigate them.
Explore Insurance & Risk Questions
Do I have enough life insurance?
Do I have too much life insurance?
Is the insurance I bought years ago still appropriate?
Am I paying too much for my existing coverage?
Should I keep my whole-life or other cash-value policy?
What happens financially if I die prematurely?
What happens if my spouse dies prematurely?
What happens if I become disabled and can't work?
How much disability insurance do I actually need?
Are my employer disability benefits enough?
What would a long-term-care event do to my financial plan?
Can I afford to self-insure long-term care?
Should I buy traditional long-term-care insurance?
Should I consider a hybrid life/LTC strategy?
Could an existing insurance policy be repositioned to help fund long-term care?
Do I need an umbrella liability policy?
Are there risks in my financial plan that I haven't adequately protected?
Which risks could do the most damage to an otherwise successful financial plan?
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When should I claim Social Security, and how does that decision affect everything else?
Social Security and Medicare decisions don't happen in isolation. We help clients evaluate claiming strategies, spousal and survivor benefits, taxes, Medicare enrollment and IRMAA while considering how those choices interact with retirement timing, investments, real estate income and other resources.
Explore Social Security & Medicare Questions
When should I claim Social Security?
Should I take Social Security early or wait?
Is waiting until 70 always better?
How do spousal benefits work?
What happens to Social Security when one spouse dies?
How should Social Security coordinate with my investments and other retirement income?
Should Social Security timing change when I retire?
How will Social Security be taxed?
When should I enroll in Medicare?
What is IRMAA and could it affect me?
Could a Roth conversion or other income decision increase my Medicare premiums?
Should I try to maximize my Social Security benefit, or maximize my overall retirement plan?
Estate, Family & Legacy
How do I make sure what I've built supports the people and causes that matter to me?
Estate planning is about more than documents. We help clients consider how investments, real estate, beneficiary designations, family support, charitable goals and other assets fit together, and identify where coordination with an estate attorney or other professional may be needed.
Explore Estate, Family & Legacy Questions
Do I need a trust?
Is my existing estate plan still appropriate?
Are my beneficiary designations coordinated with my estate plan?
What happens financially if one of us dies?
How do I make things easier for my spouse and children?
How should real estate be handled in my estate plan?
How should business interests be handled?
Is my estate potentially subject to estate tax?
Should I give assets to my children now or leave them later?
How much can I give my children without jeopardizing my own financial independence?
How should I plan for a child with special needs?
How should we help aging parents?
How should an inheritance change my financial plan?
What's the best way to incorporate charitable giving?
If something happened to me tomorrow, would the people I care about know what to do?
Business Owners
Is my business building my financial future, or is too much of my future dependent on it?
For business owners, personal and business finances are often inseparable. We help clients consider cash flow, retirement savings, risk, insurance, business value, debt and eventual transition or sale while building personal wealth and financial independence outside the business.
Explore Business Owner Questions
Is my personal financial plan too dependent on my business?
How should I coordinate business and personal cash flow?
Am I paying myself appropriately?
What retirement plan is best for my business?
How can I potentially contribute more toward retirement?
Should I consider a Solo 401(k), SEP IRA or cash balance plan?
What happens to my family if I can't work?
What happens to the business if I die or become disabled?
Do I need key-person or business-overhead insurance?
How should a buy-sell agreement be funded?
How much business debt is reasonable?
How should I prepare financially for eventually selling the business?
Am I building personal wealth outside the business, or is nearly everything dependent on it?
Education & Helping Family
How much can we help our family without compromising our own financial future?
Helping children and grandchildren can be an important financial goal, but it needs to fit within the larger plan. We help clients evaluate college funding, 529 plans, student loans, gifts, home purchases and other family support while considering the impact on their own retirement and financial independence.
Explore Education & Family Questions
How much should we save for college?
Are we on track?
Should we fully fund college or expect our children to contribute?
How do we balance college funding with retirement?
Should we use a 529 plan?
What happens if there's money left in a 529?
Can unused 529 money eventually be moved to a Roth IRA?
Should we pay our child's student loans?
Can we afford to help an adult child buy a home?
How much financial support can we provide without damaging our own plan?
Should we fund education for grandchildren?
When does helping our children begin to jeopardize our own financial independence?
Major Life Changes
Something changed. What should I do now, and what shouldn't I rush?
A job change, inheritance, property or business sale, divorce, death, illness or relocation can create several financial decisions at once. We help clients identify what needs immediate attention, what can wait, and how the change affects the rest of their financial plan.
Explore Life Change Questions
I was laid off. What should I do first?
I'm changing careers. How does that affect my plan?
I received an inheritance. What should I do with it?
I'm selling a business. What should I be thinking about before the sale?
I'm selling a major property. What decisions should I make before closing?
We're getting divorced. What financial decisions matter most?
My spouse died. What needs attention now, and what can wait?
Someone in our family has become seriously ill or disabled. How does that change the plan?
We're relocating. What financial issues should we consider?
Our income has changed substantially. What else should change?
Something significant just changed in our lives. What decisions should we make now, and which ones shouldn't we rush?
What Am I Missing?
What don't I know to ask?
Some of the most valuable planning questions aren't the ones that bring someone through the door. We look across your financial life for risks, opportunities, assumptions and connections that may not be obvious when investments, real estate, taxes, insurance, retirement and estate planning are considered separately.
Explore "What Am I Missing?" Questions
What am I missing?
Where are the biggest weaknesses in my financial plan?
Where are the biggest opportunities?
Which financial decisions will have the greatest impact?
What am I doing simply because I've always done it that way?
Are any of my assets underperforming?
Is any of my real estate performing differently than I think it is?
Am I taking risks without being adequately compensated for them?
Are my investments, real estate, taxes, insurance and estate plan actually working together?
Are my spouse and I working toward the same financial goals?
What assumptions am I making that should be tested?
Which financial "rules of thumb" don't actually apply to me?
What should I stop doing?
What should I do first?
What can wait?
If I do nothing differently, where does my current path lead?
What opportunities would I see if my entire financial life were analyzed together?
Your question is a good place to start.
You don't need to know which category your question belongs in, or even all the questions you should be asking. That's part of comprehensive financial advice: looking beyond the question you came in with, testing the assumptions behind it, and understanding how the decision may affect the rest of your financial life.
