Live Q&A · June 29, 2026
Every question. Every answer.
The questions our partners and attendees put to Kim during the live session, summarized for clarity. This is educational and is not tax advice; confirm specifics for your own situation with a professional.
How much is never planning actually costing people?
Asked by Anita Akpunku
It depends on the situation, but $20,000 to $40,000 a year in savings is very typical just from the low-hanging fruit, before any investing. Some clients save hundreds of thousands. Compounded over a working life, the difference is life-changing.
If someone puts $100,000 into a multifamily deal, how big is the paper loss from cost segregation?
Asked by Leah Krebs
Typically around 25%, give or take, so roughly $25,000 on a $100,000 investment, allocated to you per the operating agreement.
Why is one apartment building better than several single-family homes?
Asked by Fedna Morency
More to leverage: multiple tenants so a single vacancy is not a 100% loss, economies of scale, easier financing (you can refinance by unit), and more built-in equity. Several single-families can get close, but multifamily achieves it with less vacancy risk and more ease.
As busy medical professionals without time for REPS, how do we still get the savings?
Asked by Anita Akpunku
Doctors almost never qualify, not mainly because of the 750 hours but because real estate must exceed the hours you spend in any other income source, and physicians earn more from medicine. The workaround is a spouse qualifying. "If any tax professional ever tells you that they'll take that REP status for you, that should be a pretty big red flag."
As a full-time physician who cannot spend 750 hours, is there another way to use real estate losses against my salary?
Asked by Dr. Kirk Campbell
Yes, a short-term rental is the easiest unlock. It requires material participation but not much time (answering renter questions, facilitating fixes, working with a manager). To count as short-term the average stay must be 7 days or less, with at least two rentals showing income. Long-term rentals are capped at $25,000 a year per property.
Which strategy gives the best bang for the buck in year one?
Asked by Dr. Kirk Campbell
If you have a passive-loss offset (a short-term rental or a spouse with REPS), the cost-segregation study is the biggest. Without that offset, a non-professional with a long-term rental is capped at $25,000 per property, so the 1031 exchange becomes the biggest lever because it defers all of the capital gains.
Who initiates the cost-segregation study on a multifamily deal?
Asked by Leah Krebs
The owner of the property or partnership initiates it, and a good tax professional should recommend it. Doc Wealth provides a referral list of engineering companies to choose from.
Can taxes "disappear" if you pass the property to your kids?
Asked by Fedna Morency
Not entirely. Depreciation recapture is normally taxed at your marginal rate. A step-up in basis at death converts it to the lower capital-gains treatment, and heirs can then do a 1031 to defer further. It lowers the tax substantially, but it does not erase it outright.
How can you invest in real estate inside a cash balance plan?
Asked by Dr. Ntiense Robin
By self-directing it. Instead of holding stocks, you self-direct the plan, make the purchase, sell later, and roll the proceeds back into the plan (kept at arm's length). The money keeps growing inside the plan. "That's actually how Warren Buffett got as rich as he did, through his cash balance plan."
Outside of real estate, what is the most common tax-saving move high earners miss?
Asked by Edwin Valverde
Oil and gas investment. Investors typically deduct 80% to 90% of the investment in the first year via depreciation, depletion, and drilling costs, and those losses can offset active earned income. The back-end ROI is also tax-advantaged.
As a 1099 earner, how far can deductions go before raising IRS flags?
Asked by Edwin Valverde
It is not the number of deductions, it is the percentage of each category versus your gross revenue. The IRS keeps a database of normal expense percentages by business type. Claiming 30% rent when 10% is typical, or 40% marketing when 5% is typical, is a major flag and is how fact-based (non-random) audits are selected.
For a practice owner, how much can the right business setup save, and is it worth the paperwork?
Asked by Blaise Nzeda
A big difference. Above roughly $80,000 of net income, an S-corp election starts saving meaningfully, easily $5,000 to $6,000 or more a year for a typical practice, because distribution income is not subject to self-employment tax. One caveat: some states penalize S-corps.
With the Augusta Rule, do you rent the whole house or a room, and how do you set the rate?
Asked by Dr. Ntiense Robin
It is about the type of event, not the room. For a large gathering, pull comparables from event centers or hotel ballrooms; for a smaller meeting, use hotel meeting rooms or coworking spaces. Deductions can run $600 to $1,000 or more per rental, totaling roughly $11,000 to $14,000 across the year.
If I own an LLC and do 1099 work, how do I write off my car payments?
Asked by Salvador, an attendee
The principal of the payment is not deductible. You write off the vehicle either by actual expenses (gas, repairs, interest, depreciation) at your business-use percentage, or by mileage (about 72.5 cents per mile this year). To take 100% of the purchase price in year one, the vehicle must be over 6,000 pounds.
Are there tax benefits for someone with a busy job who just wants to invest in real estate, with no time for another role?
Asked by Dr. Kirk Campbell
Yes, options that do not require hours: REITs, Qualified Opportunity Funds (hold 10 years and pay no capital gain on the sale), and syndications. In a syndication, if a cost-seg is done at the entity level the losses pass through to you, and as a passive investor they accumulate and carry forward, typically reducing taxable income to zero without a negative hit.
What is the most common mistake smart, high-earning investors make?
Asked by Blaise Nzeda
Backdoor Roth conversions reported incorrectly, which are costly and time-consuming to unwind. The fix is working with a well-seasoned professional. The other mistake is simply waiting too long to start, people kick themselves for not doing it sooner.
If someone takes one thing from tonight and starts this week, what should it be?
Asked by Leah Krebs
Get with a proactive tax-planning professional you trust. Reactive filing only tells you what you owe; the investment vehicle does not matter nearly as much without a seasoned planner on your side. "Tax planning is really where it's at."
