All Forum Posts by: Aaron Zimmerman

It’s certainly possible to get material participation and be a real estate professional but what might be better is your husband becoming a realtor if that’s of interest. That would make qualifying for reps easier and you can continue the plan with managing your rentals. I would firm this up with a tax professional to make sure you’re implementing the strategy properly. 

Kathy - you’ve come to the right place. There are about 20+ accountants in here and growing that provide the exact services you’re looking for.

One tip in your search, I’d recommend working with a cpa that is looking through your books (even at year end) and making sure you’ve gotten all of the appropriate deductions. Biggest items are mortgage interest, property taxes, insurance, and capex/repairs.

Yes - as others have mentioned, a little tough to advise when we don't know how much income you make. I saw someone say OP made $35k. If that's the case, I would use excess savings towards investing in skills that will increase income in the next 5-10 years. Hopefully as income grows, I would look to get into long term rentals via house hacking or partners. House hacking will allow you to purchase a house and have the rents of the other units offsetting your mortgage and will help with DTI.

Great tips! Thanks for sharing.

I would recommend trying to save as much as possible over the next two years. As needed, purchase items that will further your education that will make you more aware of mitigating the risks of purchasing property. 

@Daniel Bourdeau - thanks for sharing this information. As someone that lives in Chicago, this is very encouraging news. Glad to hear you're having success here and appreciate you spreading the good word about Chicago. 

I would consider hiring a bookkeeper after 5 properties/when bookkeeping becomes too big of a time burden/you become out of your depth. 

I would hire a tax accountant as soon as you buy your first property. A good tax accountant can find additional deductions/ask questions that may unlock additional deductions. 

It depends what your goals are with maximizing bonus depreciation. You can always do a cost segregation on one property in 2025 and then on a separate property in 2026. Of course, you'd need to meet the STR loophole requirements in 2026 as well.

I would talk with a CPA, make sure you meet the requirements of STR loophole, and then plan accordingly with the right strategy. It will be well worth it.

With this property, is there an opportunity to increase revenue/increase occupancy? Before selling the property, I would make sure you did everything in your power to maximize revenue. Perhaps there's some opportunities with marketing or other means to increase occupancy and revenue of the property. 

If you do sell, I would ask your CPA to walk you through the impacts BEFORE you sell. You always want to know what you're getting yourself into. Then, you can assess if 1031 is even a viable option.

I have house hacked on the Northwest side of Chicago. It is a lot tougher now than when I started. You would have to get creative to cash flow for sure but it seems like you have the right ideas with rent by the room. @Victor So is the best person I know that has maximized cash flow through creative means.