Your first hire is unlikely to work out though, was you won't have a good hiring system in place. - So, recommend having that first hire document the crap out of what you want them to do.

I am trying to find a mentor and have a relationship that I think will work out well.

How did the cash flow work out?

Just don't be an idiot with your finances and it'll all work out. 

Long term thus city will work out its issues.

We have 3 boys who are actively in sports and the location of the house just doesn't work out for us. 

The issue there is that you have some people that just don’t work out and some people you have to let go.

Okay pal, go with them I am sure it will work out the same (sarcasm) (hangs up phone).Like anything in life, you get what you pay for. 

That is something I would for sure have to look into as, according to your post, it seems like the timeline for mid-term rentals kind of lines up with the amount of time that we would be gone each year, which would work out well and probably require less of a hassle of trying to maintain the property after each stay for Air BnB.

Hate hearing that it didn't work out for you on that one.