You will get pushback from GCs on this so be prepared to obtain several estimates and have several conversations before finding the one you ultimately hire.3.

For example, you could increase the rent by $250 now and the remaining $250 after six months.Just be prepared for the possibility that the tenant might not be able to afford the new rent.

If the leases are to terminate a month after closing, you should be prepared for the possibility of vacancies.

Maybe it’s the case that you can dispute the appraisal a bit and find better comps if you truly believed you were shorted on the value and also the rent, but be prepared that by providing other suggestions to an appraiser may not ultimately yield you any success because what’s happening is basically telling appraiser that they are bad at their job.  

I see similar listings up for $100-$180/night.I am preparing to get the property ready with about $3k in furniture, dishes, linens, and everything else to make it ready.

It is hard to prepare for me because I do not know if my next project is in 6 weeks or 6 months so interviewing now is sort of pointless. 

Now, I am preparing to file an eviction case.

You can't count on believing that the family member will not produce a handwritten lease (real or not), or other paperwork & tactics, to throw a big old wrench in your initial/expected timeline.You CAN expect that if they see you as the big old rich/developer/bad guy enemy, they will do as much damage as they can, and drag their feet as long as possible.See if you can feel out what the relative actually wants/ needs, connect/come prepared with info on resources for local "housing help" options, etc (perhaps), and figure out what you can do to solve the problem (cash for keys with an incentive for quicker move out timeframe?

You aren't prepared to go "all in".So, no money, no willingness to convert equity to money, leaves him with nothing he can do for you.

Your tenant sounds like a good tenant otherwise, but you should be sure that your jurisdictional rules changing from a term to M2M do not change in a way you are not prepared to handle.