Going to walk in his office and talk to him face to face. I

The biggest obstacle you’re going to face is getting the realtors on board.

Hearing a lot of no's and getting doors slammed in your face is bound to wear on you over time.  

@David Affonso @Chi Wei LinI suspect that a problem you will BOTH face is that an agent who is doing it right will be spending 5x as much time on you as on a rando FTHB that just wants a pretty lawn, but the commission check will be the same.

A challenge I face is that other owners in the same building have lower or no carrying costs - some own their units free and clear or this is not their business - so their monthly and seasonal rates are significantly lower than market, which hurts newer investors who are asking fair value.

If she was already that much in my face, I can only imagine how things would have gone once she moved in.

I've found that the major challenges data aggregators face is that there are as many ways to retrieve data as there are counties in the US.

Face to face is great. 

I tend to deal with the smaller banks where I can walk into the office and deal face to face; I think the personal contact is important. 

The Dilemma I face is this: My price range is $275k - $350k, but I struggle to find something nice enough to want to live in, that would also cash flow once we move again, turning the home into rental #3.