Quote from @Hares Najand: We could dig into the nuances of all your issues, but I think it's simpler to just answer one question: do you have evidence they are cheating your or failing to protect you as their client?

It might take some digging, but with the right deal, it’s definitely possible to make it work in Jacksonville.

But once you get tenants and leases in place, lenders will really dig in to the details. 

It's great that you're already digging into the details and considering the BRRRR strategy.

I'm happy to send some articles that dig deeper into Section 8 investing as well.Best of luck on your journey!

Do you have to bust a hole in the wall or dig holes everywhere - how much does that cost?  

After digging into state requirements, I’m starting to think some of their practices may not even comply with Department of Real Estate laws.

I was excited to dig in and contribute but was immediately turned off by that price.Some other will probably feel different.

I have done quite a bit of digging and I've been told by multiple agents that these are the only two that don't have rules against STR.If you're serious about going this route, I believe that these two buildings would be a good place to start.Also, if you're not completely set on the buildings being full amenity, I agree with @Michael K. that you can find some multi-unit gems in great neighborhoods and operate them as STR buildings.

If you dig in on the south or west side, you should be getting deals that are distressed enough to just use regular hard/bridge/private money that is expensive.