There are a lot of trade-offs, complexities, and expenses involved that can effectively cost more than the amount of tax being paid on UDFI by an IRA. 

How many times is your loan going to be traded to get to the end buyer.

A real property trade or business is broadly defined to include real property development, redevelopment, construction, reconstruction, acquisition, conversion, rental, operation, management, leasing, or brokerage [IRC Sec. 469(c)(7)(C)].

If you're a carpenter by trade, you may be short on money but have a lot of skills useful for flipping or renovating fixer-uppers.

The Chicago Neighborhood Initiative has rehabbed a decent amount of homes on Champlain and Langley, and 30 more distressed assets will be coming alive shortly, so there is progress - https://www.chicago.gov/city/en/depts/doh/provdrs/housing_resources/news/2020/july/city-grant-approved-to-restore-30-historic-pulman-rowhouses.htmlYou are right, inventory is extremely rare down there as it's tight-knit, not a lot of trading, and when it does, owners tend to trade with each other.

The trade off here is that investing in RE is more work than stocks. 

He is more knowledgeable and has connections with trades. 

The new CPE (core inflation) and CPI inflation numbers just released on thursday so its your lucky day and rates have dropped to the lower 6's (prior was around 7 or little over - range).Once monday mortgage bond market opens at 630PST or 830 CST yourtime you'll have different pricing so definitely check in on monday and to accurately compare you'd need to get everyone's quote at the same time and same day because the mortgage bond market trades in real time and could reprice multiple times perday.In the end most lenders should be so close that you'll want to work with the best you can find.Hope that addresses the real life situation of conventional mortgage pricing (bank and portfolio mortgage prices change a lot less frequently and is another topic for another time).Best Regards,@Matthew Kwan@Carlos Valencia

I trade rent for 12 hours of handyman services per week-- but I wouldn't do that until you find a really trustworthy handy person.

Challenges - Since this was our first property, we did not have a contractor, plumber, electrician in place and finding these trades was challenging as these trades are extremely busy at this time.