All Forum Posts by: Aaron Zimmerman

You will want to work with a CPA that will walk you through material participation and other requirements. Great record keeping is imperative if you're trying to utilize the STR Loophole.

@Christian Artuso - check out the straight up Chicago investor page for events in Chicago. They have a pretty robust list. 

Jack - there's a listing of all the major meetups on the straight up Chicago investor page. I'd personally recommend Windy City REI and Chicago Multifamily Club

@Nicholas Bond - there’s a lot of great real estate CPAs that are on BP. I’d recommend searching through the forums and reaching out to a few. Given the time of year, time is of the essence. 

Michael - if you’re open to expanding your search nationally, there’s a lot of great CPAs on here that can handle this filing. There’s quite a few good CPAs that are in this forum. I’d recommend reaching out to a few. That said, time is of the essence. 

Yes - income level would be important and to know what your losses are without bonus depreciation. 

What you don’t want to do is to do a cost segregation study and then not get any benefit. Get your cpa to explain why they think a cost segregation study isn’t beneficial in your situation. 

Ross - there’s lots of great CPAs on here that can help. You’ll want to make sure your cpa is well versed in short term rentals. 

Biggest things you’ll want your cpa to guide you through;

Material participation- there’s three tests; 500 hours; 100 hours and more than anyone else’s time, and substantially all the activity. You’ll want your cpa to help determine which hours count and which hours don’t count. 

Average stay - you’ll want to see how long the average stay is. It needs to be less than 7 days. 

Personal use - if you or your family used the property for personal purposes, you will need this to factored in. 

There’s plenty of great CPAs on here. I’d recommend reaching out to a few if you’re okay working with them remotely. 

Really liked this post. I thought house hacking was a great intro into properties. For many, it allows people to test the waters to see if they enjoy being a landlord. 

I think the biggest lesson that I have is to vet the inherited tenants. You want to make sure you’d rent to them again. If not, you may be stuck with a costly eviction. 

In terms of your investment, you stated that the primary reason is for tax benefits. I would caution this approach as a cpa. You want to make sure the investment is solid and then focus on the benefits. Not the other way around.