I feel like overall there is a lot of unknowns here for the reduction in interest rate to be worth the premium.

If he doesn't need the cash now, you could also negotiate a split you're comfortable with to get him the return you and he feel he should have at the point you refi when the balloon payment comes due. 

Please feel free to reach out for discussion. 

The nickel and diming has just gotten way out of control and I feel painted in a corner a bit. 

So don't feel bad, happens to us and not really for our fault :)

As an investor looking to purchase an STR in a ski town, I’m not sure I’d feel that confident in a court deciding in my favor, personally.

HelloOver saturated STR in Ohio markets have caused many STR to drastically lower costs to as low as  $100 for entire bedroom home.My are higher and I'm not competitive with the lower cost Abnbs.I also feel hotel industry are mass building new hotels to compete with str. 

I think other people seeing makes me feel accountable to post along with having it written out.

If we can help, feel free to reach out! 

Unfortunately I feel like a new roof is going to be pretty standard on the things I'm looking at so it might just have to get done on a regular basis.