Because of this, I believe the market for selling my houses is likely limited to other investors.

@Stefano Grottoli all the $1550 means with CMHA is they will pay up to that amount within Cleveland city limits.

What rent limitations are there with S8 vouchers?

Your current plan seems like a lot of sacrifice for limited gain.  

You could explore other options, but with limited income on paper, this might be your best path for now.

Iwhen underwriting we also want to know the exit strategy of the borrower to make sure they are not limiting themselves to a single exitExcellent!

Try to avoid renting out a single family to an actual family because you will limit how much juice you can squeeze from that property. 

Quote from @Ashish Acharya: @Johnny Smith With an AGI over $150,000, Passive Activity Losses (PALs) from rentals are limited, meaning you can only carry them forward without offsetting your W2 income.

So does the book provide a loophole to the three property limitation to the “mortgage origination” rule (Dodd Frank)?

Due Diligence and Feasibility Studies - What studies or tests are essential before purchasing raw land?