Your choice depends on your goals.

Jacksonville not as much as the other cities though and I would call it more like purple, with the red and blue fault lines running within the city itself.Social media is my lead gen of choice for now because it's free (except for what I've paid for BP Premium) and I've depleted just about all reserve capital I had to the point I'm contemplating taking on a day job again (with my tail between my legs having to admit that when I said I was gonna go off and be a hot shot realtor and those corporate psychopaths would never see me again, I was mistaken). 

I agree with @Ryan Kelly.

working as a server in a restaurant has never been about being a career choice. it is just a stepping stone. however, some waiters make plenty of money because of tips. an individual is the person who decides on their destiny. you chose if you will be a dishwasher for the rest of your life or if you will move onto to something else. we cannot save everyone because they make bad choices. choices have consequences.

The only choices/disagreements would be who keeps which property, what gets sold, etc.

I would just reiterate that the rate is going up X% per the terms of the lease and if they don't like it their choice is to vacate.

All of this to say you've got some great choices and for me it would come down to what I feel is the best use of the property long term.

There's a lot of choice out there. https://www.foacommercial.com/...https://lendsimpli.com/rental-...

If he is refusing to leave you may need to hire someone to kick him out and I would imagine a lawyer that specializes in this or a large property manager would have a contact for you.If the lawyer gives you the red light you really have no choice but to wait until the end of the lease term and then not renew the lease.

If she is paying it should be her choice.