I tried Guesty last year, but I had several issues with double bookings and poor customer service. 

Any current roadblocks including time-to rehab permits being issued, local landlord laws/trends, property tax to rent YoY trends, etc. 

Better cash flow, but more tenant issues in multi-family. 

If the fire department needs to siphon water from a pond or lack it impacts the ISO rating of the department.Try and find out what the issue is and share the info here.

If your market supports medium term rental demand and you're having issues getting booked, put yourself in a potential guests shoes when reviewing your listing. 

But if its humming right along and has no operational issues then your probably going to pay much more.  

Our current rent is $2600 I want to offer to pay $3000 for as long as she wants 1-15 years and then pay $600k My main question is whether that type of structure of offer makes sense legally or technically or practically. 

If you had a written lease in place double check what it says about your security deposit- even if you didn't technically have one.

Just wondering if anyone has done this and what safeguards (contract, insurance additional coverage etc), if any, they felt were necessary, and if they've had any unexpected issues.  

I have considered carpet but that won’t help with the heating issues.