I think you're spot on about not directly asking someone to be your mentor and going more for the 'let me take you out to lunch' angle.  

Most of the time if they pressure you to buy something on the spot, that is usually a red flag.  

I'm thinking SFR from 80K - 140K is the spot for me in a good location.

You're definitely in the right spot to learn any and everything about wholesaling or real estate in general.

The building was an old bar - or more like a series of bars because it was a terrible spot for this type of building.

Many of our clients will use one of those spots for a place holder - a property that might be held by a friendly party who would be willing to sell in a pinch.  

Having just spent a lovely weekend in Door County, Wisconsin and coming from the (comparatively -- okay, absolutely) pricier vacation spot of Telluride, CO, I'm wondering why such a charming set of waterside villages within driving distance of Chicago, Milwaukee, etc., should be so inexpensive!

@Inderpal Chadha hit it right on the spot.  

Natick is really a sweet spot of convenience to the city and highways, while not being outrageously expensive (although this seems to be changing day by day).

Everyone responding here is pretty spot on whether it is worth the effort to rehab in Waterbury when other CT towns have more pleasant results.