All Forum Posts by: Aaron Zimmerman

Chicago can be quite seasonal. Depending on the neighborhood, there simply might not be a lot of demand but I would not get discouraged. I’ve had to rent in the offseason before and have gotten quality applicants but it does take longer. 

I’ve had the best success with Zillow (which goes out to hotpads and trulia) as well. I’ve tried domu but haven’t had much success.

I would echo other comments about screening tenants, especially in Chicago. It can be a long time to get someone out. 

You've come to the right place as there's quite a few real estate focused CPAs here. One thing that I'd focus on in particular is the STR Loophole for maximizing deductions. You'll want to talk with your cpa about this as there are some hoops you'll have to jump through.

This is a crazy ordinance all the way around. Thank you for posting and sharing your thoughts. I hope they don’t expand the pilot area to others in the city. Thank you to everyone that commented as well. Very informative!

The biggest thing with house hacking is making sure the property breaks even when you leave after all expenses. Similar to what others said, it’s probably not realistic with current rates on most houses to live for free. The key is stack the savings. 

I would you to think long term as far as rent appreciation, insurance (which keeps ticking much higher each year), and property taxes (which may get reassessed when you purchase the property). 

Inherited tenants - vet them and look at previous records

Make sure the property cash flows after you move out

Build your team: handyman, hvac, plumbing, etc. this will take some time.

As stated by a number of fellow accountants, there are a ton on here. I’d recommend checking out their profiles and previous comments. See which ones you like and interview 2-4 and work with a professional. 

This is great! It hits the nail on the head. Only thing I’d add is between step 2 and step 3, talk with a CPA before doing a cost segregation study. An investor needs to be 100% sure they’ve jumped through all the hoops necessary.

 I would agree that RE prof status is hard to achieve with a limited number of properties. There’d need to be a lot of rehab work/managing that would require you to put in that many hours.

From a financial perspective, it seems like the highest leverage way to keep buying more properties is leveraging your W-2’s and then being work optional.
Have you enjoyed leaving your W-2? Is there a way to perhaps work part time? I think overall life satisfaction is very important so ultimately have to do what’s best for you. Biggest thing is not letting the tax tail wag the dog. 

@Jonathan Klemm - thanks for the shoutout!

This is a very nuanced conversation. The biggest thing I’d say is to not let the tax tail wag the dog. If your highest leverage activity is earning money through a w-2, then stick with it. 

When you make over $150k MAGI, you can’t take losses against active income. However, those losses do roll forward each year until the property is sold. 
I’d recommend the straight up Chicago investor podcast, tax free wealth, and amanda Han’s tax books if you want to read more about it. 

 Thank you! I’m in the exploratory phase right now and will reach out with any questions! Thank you for being a resource!