If your friend is unwilling to pay that then move on.

It would be better to open a new card with 0% interest on balance transfers, move your debt to that card, then pay it off like a mad man before interest is charged.Your scenario indicates you aren't financially disciplined.

So move forward and add whatever language is needed in the lease to deal with this matter.

I think a sale is probably the best thing sell for what its worth dont let an investor suck him into some wholesaler suck his equity from him.. sell re group and move on.. 

I currently work with investors to build their portfolios with Turn-key long-term rentals, making it hands-free for the investors. 

The number you feel would be enough to retire on will keep moving.

It depends.If you find a PM that is willing only to do some task becaue you're still very involved then go for price.If you're looking for a PM that will ease the stress to where you forget you're even a landlord then quality of service is key not price.

The key is to offer something different to the other homes, and be an attentive host, to get good reviews to boost OTA (Airbnb/vrbo) rankings. 

Have you considered Turn-key? 

This property would be my third investment so I'm undecided on moving forward.