I always assured them i would be happy to resign their lease in june/july for an additional 12 months but could not go over 6 months at this time...

Does someone who's done this many time before have a series of questions that they make sure to answer to assure themselves they understand the area dynamics?

Anytime returns are too good, an investor needs to really be on alert and use common sense.Even with the past few years in mind, we can assure ourselves another bubble will happen again somewhere down the line.Ryan

And as @Steve Babiak said, any contingency you can waive either in the contract or via verbal assurance helps.

We had a great friend and realtor who assured us these first few properties were going to cash flow, and we jumped in.I remember pulling up to the first property after we closed on it, and having butterflies in my stomach as I walked up to introduce myself to the new tenants.

What can i say to this seller to assure him im only trying to help?

So he would also not fit your "blind, physically crippled, or in any other way in true 'need' of service animals" but he most assuredly needs his service animal and receives great benefit from it. 

Now just need to couple yourself with a TK provider that meets not only your criteria, but your culture of thinking, assuring you that your asset is being well cared for with foresight and ran as a business. 

I don't think you can apply for a zoning change until you own the property so it may be a lot of phone calls with little or no assurance.

until then...out of state is awesome.As a Hawaii investor going back to the 70's I can assure you that prices have been going up like crazy for decades.