You want to appeal to the most people and many buyers will want to live in the home, so having tenants will limit who it appeals to.

Hoping there is an opportunity despite my limited capital

What you can do to offset this profit is to invest in syndications that do cost segregation studies (which will lower your tax you pay).

I get applicants with limited to no rent history many times because they are young and just don't have the history.

This dynamic needs to change and hopefully difficult times like we are currently in will force limited partners to demands more transparency. 

Print them off, study them, highlight them, make notes, read some blog posts, and understand the subject.The second document he links includes precise definitions and a guide for landlords to use for screening support animals.

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.