You owe money secured by property; you don’t pay when owed, you lose property.  

If I did decide to go this route, are there any pro tips anyone can provide on what I should screen for during the tenants application that is more specific to dealing with housing voucher applicants?

Your 50% value would need to be equal to or greater than the value of your relinquished properties (same with the debt that was paid off if any) @Dave Foster can provide more guidance. 

For example, you can put in your advertisement that all applicants must make 3x the monthly rent, have a credit score of 620, or provide a recent landlord reference.

If you find a cleaner to manage it life is easy but it's also difficult to maintain because you lose them to others that can provide more consistent work.  

The pay at it was so low it wasn’t helping provide down payment money but it did cover my cost of living.

With those stats, you'll pull half the accountants in the forum out of the woodwork, most of us would be more than happy to work with someone in your financial position as it means we can provide a fair amount of value.Whoever you work with, I would recommend you consider finding a firm with substantial experience to offer in both real estate, and estate/gift planning given your goals.. 

Plus, insurance premiums are expected to go down by up to 50% due to the El Niño effect, which means fewer hurricanes are expected to hit Central Florida, and new legislation reducing fraud provides another great advantage.

Networking with experienced investors can provide invaluable insights and guidance specific to your market.Property Search and Due Diligence: Once you're familiar with the market and financing options, start actively searching for suitable duplex properties.

If you meet this regulated threshold at the end of the year, an IRS 1099-K tax form will be provided to you."