I’m also planning on climbing MT Washington and riding the sherb down if anyone is into skinning or climbing hit me up!

Sounds like you are willing to go to work and let your daughter take a free ride.

Ideally, I'd like my next property to be closer to work so I can ride my bike to and from work and just buy and hold this property.

Buying and selling is a roller coaster ride for sure.

Although as I am thinking about it @Chris Clothier  has done some data mining and posted it on BP about how well his companies owners do .. with big data like how many turn overs.. how many owners own how many properties etc etc.I know Chris will agree with me on asset class though.. most turnkey companies will also move up in asset class.. many starting off with low value .. then realizing how hard they are to work.. say heck with that we are going to sell top end stuff and I think that's kind of were MI morphed too at least it appears that way to me.

The tenant can skip getting his account and ride on the winter program and not pay the bill till they get caught and the pipe freeze and you have no idea if they are paying their bills as the Utility companies don't even share info on the status of the account since it is not yours as a land lord. 

I have been riding around in different neighborhoods, and looking at different real estate sites like Redfin, Trulia, and Zillow.

Once you found the person(s) for step 2, ask you you can ride along with him for a day.

If you have significant reserves you can potentially ride it out. 

I loaded up on 4 plexes in Montrose in '06 (about $6MM worth) riding the 12-14% appreciaition wave thinking it was never going to end.