Since the bills are sent to the service address, I wasn’t aware of the situation until now.I’d like to arrange for a plumber to diagnose the leak, but with the water shut off until the balance is paid, I’m unsure how to proceed.

I also had two separate licensed plumbers check the plumbing for leaks and there are none.

The con is obviously the cost because in addition to waiting a long time for permit, it requires serious structural changes + roofing, etc. 

Of course capex does come into play, but I have a lot of factors on my side including most major components of the property have been replaced already, including roof replaced 2 years ago, water heater replaced 3 years ago, full house was just repiped, septic system is 5 years old, HVAC system replaced in last 7 years, i do not cover appliances with warranty in my rentals, and the tenant I placed in the property is a single dude who works 60 hours a week and just needs a place to sleep.

Roof?

I had some minor water leaks and some subfloor issues that overall did not amount to much, but I had to have an vacancy to fix later.

You’ll reverse engineer top-performing properties and get title & description recommendations, discover rare amenities in your market, & utilize competitor’s reviews to convert more guests.My expertise is in increasing visibility in search engines (and lead generation for law firms, roofing companies, etc) and not the AirBNB/VRBO algorithms.

 @Nathan Gesner Funny you should say that as that is what we did yesterday ..we actually lowered it to $1685 and it looks like we have a renter  hopefully  ( fingers crossed ).Income verified , credit score etc It’s a bit low for me but we can get the mortgage paid, the heloc payments and the roof payments and still put some cash flow in  reserves each month as we will pencil out a bit.

Why is the roof ok to do while they’re in there still? 

I have no prior claims and the house has new flooring, new roof, new everything.