I feel like there will be a flip opportunity or some ways to do some business together.

There could be negligence on your part for failing to maintain them.

Or just hold on tight to my standards even if theres a vacancy? 

This was a bit of a let down hearing all of this, since there don’t seem to be many duplexes or front houses with in-law suites that would serve the same purpose.Is there something I’m missing?

He's playing with numbers, I reckon, and I bet there was a mortgage on the property, so his cash in was not $230k.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

There are a few in my town and I am confident I can do a really good Airbnb, but even with all the research it scares me that I would not make enough on short term rental market to cover everything and make that extra money necessary.

There are landers that will be able to cross collateralize the florida portfolio for the downpayment.  

So I am weighing my options on whether to keep going with eviction by involving an attorney or there could be alternative work around. 

I have a great property management company I use there- they do section 8 well.