I think chatting with hosts is the BEST way to get sound and clear cut data (given they keep P/Ls, etc.) because I know I've heard from some folks rumor the idea that Airdna skews data a little bit to make numbers look better than actuality to encourage folks to invest in the area & use their platform to see data.

Your clients should focus on properties with significant equity potential and work with experienced contractors to stay within budget and timeline—especially with borrowed funds on the line.Avoiding Bad Deals - Encourage them to work with experienced agents, contractors, or mentors and always run multiple scenarios, including worst-case outcomes, to stress-test their numbers.Reserves - Advise your clients to keep a reserve fund separate from their loan for emergencies, unexpected expenses, or delays.

If there's a lot more headache- then I encourage you to implement or improve a Complete Household System, try to get SFR's with 6-11 bedrooms, no more than 3 rooms per 3/4-Full bathroom, and make sure there's one (not more than one) beautiful living room with a big screen TV. 

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

I had thought as much but it's encouraging to hear from an experienced investor.Two, it sounds like talking with a CPA is an absolute must on the tax implications of this deal!

Everyone's kind of saying the same thing here so that's encouraging! 

I encourage you to consult with a qualified attorney to ensure this agreement complies with applicable laws in your area.

Encourage him to build credit to 680/700+, get 20% down, and have 9-12 months reserves and then he can get a No Income loan from one two different lenders. 

Let us know how it goes.I provide my screening criteria on my website, and I encourage applicants to screen themselves before applying so they don't waste my time, their time, or their money.

Better yet, encourage her to make a clean break....perfect time for a fresh start.Also townhomes are rarely a good investment vehicle.