Creative ways to evict a manipulative tenant?

[David D'Louhy]

I am looking for creative ways to help a family member evict a very problematic and manipulative tenant in Florida. 

Tenant received a $30,000 loan from landlord and hasn't made a payment on that in at least a year. Tenant owes landlord over $10,000 from credit card charges that were agreed he would pay back. Then when landlord died last year, he did another $6,000 cash advance the day after he found out the landlord died. Now, the widow is left dealing with the mess. Tenant shows up at landlord's memorial service and criticizes the family of the deceased. Tenant in the last 2 weeks has claimed landlord agreed to rent a property from Tenant and owes Tenant over $100,000 for it (no mention of it in previous 8 months since Landlord's death). Countless more headaches that are too numerous to mention.

In addition to the above being a pain in the neck, here are the ways I believe the tenant has defaulted on their lease. Tenant is regularly a month or two behind on rent (currently hasn't paid July or August...more on this later). Tenant has denied access to landlord and representatives who need access to the house (contractors to repair things and realtor to show the house to prospective buyers). Tenant has altered the house without permission (including but not limited to removing all smoke alarms). Tenant has done significant damage to the house. 

Tenant wants to buy the house (he has been rented for 6-7 years), but he wants to pay much less than the home is worth, AND to buy it subject to the mortgage. You can imagine with his history of not making payments, that a subject to sale would be a nightmare, so widow has turned down his verbal offer.

Now tenant has blamed landlord (widow) for not taking care of the house and gotten an attorney, told the sheriff, and the city, getting orders to fix things that he has done wrong. One of the things being ordered to fix is installing smoke alarms (which Tenant removed). He says he isn't paying rent because of the issues. My concern is that a lawsuit is coming very soon. I had recommended that family member sue tenant back in January, but they wanted to think the best that he would eventually pay back the loan.

Widow has had a listing agreement with a highly recommended Realtor for 3 months and the house isn't even on the MLS yet. The one time Realtor got in the house, it was a hot mess, so the pictures they took for the listing were kind of pointless. They tried to show it to someone they knew was interested last week and couldn't even get in.

I live 10+ hours away and have 3 kids at home, so I can't easily drop everything to go grind this out. Widow lives 4 hours away and she is tired of this tenant, but it seems like when she tries to do something, Tenant manages to delay, stall, change topic, complain about something so that Landlord can't move forward. 

Realtor is also functioning now as Property Manager and widow now has an attorney as well, however they still haven't seemed to get anywhere in the last 10 days. In my knowledge of the Tenant, he is very sneaky and manipulative, so perhaps he is just a really gifted con-artist. What are some creative ways to evict him so my family member can finally sell this house? (negative cash flow even when he does pay rent)

Besides the few things above, I also wondering if having someone buy the house subject to would at least mean he would have to get out. Does it matter if it is a family member (or an LLC owned by a family member)? However, the lease says that tenant must be gone by 60 days after a sale. I can't believe that got into the lease. That would give Tenant plenty of time to sue widow (home is in her name). I wasn't sure who would buy the house without being able to get inside (he has denied entry to people a few dozen times) unless it was at a ridiculous discount so that it would be a massive short sale. Obviously that isn't good for the widow.

Thanks in advance for helping a widow before she gets sued by this con-artist.