Also, some states view a vehicle as essential to one's livelihood and either severely restrict impound rights or grant additional rights for defense of property even if a loan is in default making said impound extremely risky.

The restriction is that you can only have 1 FHA loan at any given time (with some exceptions).

I'm not familiar with the Homeready program, but from my brief research it doesn't look like the program has that restriction. 

I hate co-ops and their boards of old, dumb busybodies who can't add 2+2.How much is your monthly maintenance fee at the co-op and what are the Board restrictions on rentals?  

What kind of hidden obstacles are there  such as zoning restrictions?   

I worry about city/government restrictions on short term rentals, but am not familiar with current laws in Chicago.

Below is what you need to know that underwriting and programs guidelines don't tell you when considering a 223(f) apartment loan.AdvantagesHighest LTV in the marketEliminate refinance and interest rate risk with fixed rate terms up to 35 yearsLow fixed rates based on GNMA securitiesNon-recourse and assumable - makes for a great exit strategy especially in a rising rate environmentNo defined financial capacity requirementsNo geographic restrictionsNo minimum population requirementsSupplemental financing availableDisadvantagesLonger processing times - 120 days at a minimum (6-9 months is typical)Higher fees - HUD and FHA fees add to the overall cost of the loanMortgage Insurance Premiums (MIP) - Initial and annual premiumsAnnual audited operating statements requiredReplacement reserve escrows requiredHUD property inspections requiredOwner distribution restrictions and Cash out restrictions 2x a yearProperty condition is important to HUD, both during initial underwriting and over the life of the loan.

You can control and budget your own CAPEX some for interior elements (like your own floor laying and the above schedule, for example) but for the association not so much.Condos are odd ducks, too.

This may not be ideal, but it is one way.The other way would be to work with a lender who has access to Non-QM products, and whose overlays do not restrict the number of financed properties allowed.

However, it does limit when it must be returned (within “a reasonable time” after a tenant moves, usually 21-45 days) and sets other restrictions on deposits.