And you have taken the extra 150 hours required for the broker's license? 

Since you already have experience with both short-term and long-term rentals, house hacking a duplex could be a smart next move.

If anyone has advice—whether it’s general tips or insights about these markets—I’d really appreciate it! 

Show the math on paper.

Location is the most important issue.  

Depends on the unit that we are renting.

I do the same tropes of things in the Tampa Florida market.  

The ability to effectively self manage would depend on the scale you are trying to buy. 

The program is designed to assist low-income families, and these benchmarks might exclude a lot of qualified people.That said, the requirement for stable rental and work history is reasonable, but you might consider relaxing the credit score or income requirements since Section 8 guarantees a portion of the rent.

Use the brokerage account to fund the downpayment and repairs to bring it up to the comps in the area.