In efforts to get more experience with IOS, we are seeking a financial partner that potentially has experience with this asset class. 

Those with little to no experience should have even larger amounts of reserves in place before they purchase real estate. 

Secondly, you'll definitely want to confirm with a tax strategist with experience in the STR space to confirm if the setup you describe will pass as an STR with the IRS. 

You can also expect increasing HOA fees, and there may be some problems renting a property inside a difficult.You don't have any experience, prices are at an all-time high, and rates are also high. 

In my experience, cost segregation studies are a lot less than $10-15k especially for smaller properties (6 units and below).

It is my understanding (per our zoning attorney) that RT4 zoning should allow 3 units but whether the current construction of the building makes that viable or not is an issue.Not an expert by any means - just our experience with zoning and digging out basements in Chicago.

@Aubrey Eblin Thank you very much for sharing your experience with the Rent To Retirement Academy. 

I'm looking to connect and network with other investors, contractors etc who have experience in this market. 

Regardless of legal nuances, I can tell you from extensive professional experience: Don will WIN an IRS audit for his Subject-to interest, as long as he can show that he made the payments.

Anyone else have experience with this?