I would be happy to talk more about locations/communities in the GS/OB area. 

I began building relationships with them by taking them out to lunch, talking about Real Estate, and just asking them if they would be willing to fund deals for me if it made sense.

You can (delicately) begin talking to these tenants now that you're in contract.

Things like landscaping/snow removal and labor cost for repairs are going to be highly variable based on your market so you'd need to do your own research on the going rate by either talking to other local investors, running your own google search, or exploring basic services on thumbtack/angies list etc. 

Next week talking with financial advisor to move from a broad approach to more food or consumer perishable goods, medical portfolio.  

Those are the people you want to talk with about this.

Are you talking about my mortgage balance currently?

The first international route from Houston to our local airport opens in April of next year, so we're going to heavily target US buyers.

(I'm not trying to talk you out of it!)

So, for items #1 and #3, I would talk to them directly first because I like to treat people like people and communicate directly about anything.