So I question if your money goes further local or OOS.  

Attend a Meetup in your area or meet someone local and grab a coffee or a beer.5.

3) Check out some of the local meetups that you can find in this forum!

You should check out CFRI, the local chapter of the National REIA.

With local home and land prices so expensive, I'd like to explore building a Tri or FourPlex on the back half of the lot. 

I recommend spending a couple nights in the unit so you have the perspective of a guest to notice anything you are missing or need and develop a check list for your cleaners and/or property manager.Your agent should be advising you on all of this and more and have local contacts for you. 

I'll usually go there first to get a baseline and then further refine that with local listings, etc.. 

We went around and spoke with about 5 local builders and visited their sites, did walk throughs, etc...

To your question Why in the area, with no experience in it I thought starting local would make sense.

Annual increases in keeping with HUD's fair market rents build in a stable increase in revenue.Regular inspections from the local agency provides us with an excuse to get into the units to check for maintenance issues that often go unreported and cause more damage.We love the model.