I think maintaining open lines of communication with the tenant and family will help the situation tremendously.You're taking a gamble, but it's one I would probably take too.

Second, if they've been there forever,  do u want to gamble a possible long term tenant but with low rent or higher rent with possibly a lot of turnovers? 

It is a quadraplex and so if I got a full occupancy then all the effort will have ben worth the gamble.

Your business is not worth taking unnecessary gambles unless they are the last tenant on earth.

Which group has the characteristics that better match your investment goals and strategy? 

Aside from that, I'd prefer a known good tenant over a gamble any day.  

If it's a wash, or an unknown gamble, then you are wasting your time to do any more to the property.It's a tough decision only you can answer but right now it's costing you more money to hold. 

It's a gamble, though.Just be sure what you do is legal.  

Then, he'd tell me that so and so had been gambling, and so and so is into porn, and so and so got a rabbit, but we can't kick her out because then we'd have to tell her we found out by going through her garbage.  

Or, the Landlord can take possession and charge them rent until he finds a new tenant.Requiring giving the tenant the choice of a termination fee or gambling on the other landlord options, is actually a tenant-friendly move for FL.