The only negotiation with the tenant after the judgment is the payment plan for the money owed to you.

So she's just behind in her mortgage and probably has a notice of default or whatever the procedure is in Florida.Your ability to get a loan for the home has nothing to do with her payment history on the home.  

He was playing nice, but then started to really press me about the final payment which was a large sum of money.

If it is accrual, then when you actually make the payment does not matter.  

He took a 401(k) loan to fund the down payment on a four-unit building in a rapidly appreciating neighborhood.

So I don't want to spend $90K on a down payment and closing costs and only have $25K to fix it up.

Get listed on all the OTA’s and a direct booking site, use good management software like HostAway, use dynamic pricing software like pricelabs, use WiFi enabled smart locks like Schlage encode, use an email capture system for guests to login to WiFi like stayfi, use those captured emails to do marketing for your direct booking site, and automate scheduling and payments for cleaners and maintenance.

The ground floor has gas hookups for a gas oven and that floor has its own gas range/oven and kitchen which is also controlled by a ground floor sub-panel also with access to the backyard and to a lower cellar area where they have their own washer dryer and storage area.   

It 12 years, assuming you make no extra payments, you'll have a paid off condo that cash flows a lot better. 

After they asses what all needs replacing or what they feel needs replacing they'll submit to you what they're willing to cover and deductibles and payments etc.