Condos don't appreciate at the same rate as single family homes, and you are always a newly elected board away from STRs getting banned in your building. 

Keep in touch with your lending partners for each one so you can understand whether you need departure residence income to qualify for the next or not.Finally, if you're investing with a Significant other, I recommend considering a "leapfrog" strategy where you buy one, then your partner buys the next, and so on.  

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

I like subto because I cant qualify for an investment loan right now so its a huge benefit, also lower buy in than an investment loan but I agree with you that its not that hard.

I've received apps in the past where this was the exact situation only for the borrower to not qualify and be stuck. 

Quote from @Don Miller: Update:Digging and form boards placed, ready for underground plumbing. 

Quote from @Dito Calderon: Sharing another update after the planning board meeting on April 1st.  

This is being built /designed for this use but somewhat like a boarding house.

At the beginning, it may be difficult to get a more expensive property that will appreciate well and so your choice is go with the cheaper property and get cash flow until you can sell and upgrade, or wait for a really good deal which you may be waiting for quite a while and its possible that you will have spent so much time waiting that you could have purchased multiple cash flowing properties by the time you get a good appreciation deal that you can qualify for / refinance after the rehab. i know anyone can go out and get seller financing deals, HML, flip to build capital or whatever the case may be I am just saying sometimes those will be harder and could result in less deals overall. 

Definitely get with a qualified tax professional on this.