While you can't take forever and a day, because a desirable candidate has choices, deciding too quickly can be disasterous.

To invest in Section 8 housing, look at areas such as Cleveland, Columbus, Cincinnati, and Dayton, choose safe neighborhoods, study Section 8 standards, analyze property types, and explore financing choices.

I don't personally own any properties leased to housing choice voucher recipients but heard from others who are having trouble leasing their properties.

I am sure there are other good choices out there, but strongly recommend them.Stessa is lacking tenant communications and maintenance tracking, but overall stands up pretty well as free, or nearly free.Buildium is pricey and has a learning curve, but if you are going to exceed 20 units, definitely look to migrating to a real professional package like buildium

You have a choice. 1.

I've read everywhere that they do not.Can someone explain which one is the correct choice and if any extra taxes are involved if they need to be on the LLC?

Maximizing cashflow becomes a strategy choice that accounts for your market and tenants.

You can do a duplex though, which might not be a bad idea.With your credit score, conventional might be a good choice, you only need 5% down for 2-4 units if you live in one. 

The garden unit tenants stopped paying rent, and I had no choice but to start the eviction process, which is still ongoing.

But for an OOS investor one consideration is access to support, first of all PM & contractors, and you have more choices in the much larger Milwaukee metro area than in a smaller submarket.