If someone is coming to Danbury for STR, I don't think they are going to want to share bathrooms and kitchen.

This will let you get in the way of appreciation.Next find a situation where you can talk and learn from someone who has done it before. 

If it was set without expectation of a payoff letter being timely sent, then someon screwed up. 

If you tell someone too early you aren't renewing their lease, especially one who is aggressive, could lead you to issues.

If you don't have the relationships, hire someone who does.This is why Brian Burke can go “large corporate” while I have to stay “small private”; he has the ability to MANAGE PEOPLE that I do not.  

Is it worth talking to someone to start the tax planning convos if this is my current situation?

If you get a proven operator that offers sightly less, it may still be a good idea to stick with someone who's been around the block for a while. 

Their pro formas felt optimistic with providing 6% annual appreciation and property management that is only about 6% of rent so I take it with a grain of salt (they offer their own property management services but it has terrible reviews on Yelp so I would probably go with someone else). 

Find someone now. 

Like @Derek Brickley said, you would need to get someone who does have a W2 (maybe your parents?)