It is a good idea to raise rent every year, even if it is a small amount.

I would list it and call up commercial brokers instead, they know the tenants and may even have someone already looking for a space.

That would be within the margin of error on algorithms which is very interesting.But the ADR is quite a bit higher, roughly 27%, which would make it worth it to go for a pool place even though you might not get higher occupancy.

I have worked with alot of out of state investors some even in NYC!

Or do I have to use the title company and their insurance quote now, even if I pay cash?

Even when you do this you will regret not coming yourself to go over everything. 

To add to the current scope, we do not care for passive income, nor will we rely on it for at least 5 years, but need to break even or cash-positive at a minimum.

Even if by myself?   

In fact even with all the hassle, this has been my most profitable property because the cash flow is the highest and with all the late fees added in I actually had a decent year.

Unless the contractor has professional liability coverage, not many avenues for recovery and even then its a long and costly process assuming the carrier picks up coverage.