I live in the Philly Suburbs and have really only considered investing where I live until I took a road trip this past weekend with my wife. 

@Tyler Lee You might consider using the MBTA commuter rail, which should work well for much of downtown Boston.Go to https://mbta.com/trip-planner Enter your start and end locations and it will give you options for public transit.If that works for you, you can start looking further outside the city where prices are much more affordable.

I think we tend to trip over the word "speculation" and forfeit an opportunity which is actually not speculative by definition, but rather is based on very careful consideration as seasoned investors. 

I still trace it back to a new year's trip to Puerto Rico but maybe it was from a later stay at some hotel.

On a trip to inspect my SFRs In Georgia I took two days to drive neighborhoods in Birmingham, AL.

I share the view that is best to always make a trip to the market and meet the team you are working considering, and see the areas they are investing in. 

If they leave windows open or back entrances unlocked, thermostats turned way up when testing the heat, Fridges/freezers not closed all the way, Bring in 4 kids who are running around and knocking holes in walls and tripping down steps (that they later blame on a piece of pulled up carpet) it all falls on your dime. 

The mix is important to me because allegedly VRBO guests are more into planning ahead and ABB guests are more into spontaneous trips, as reflected in the fact that VRBO dominates my bookings in the summer, but ABB does the rest of the year.

On my last trip it looked like the city government was doing a great job building commerce and supporting businesses.

I am planning on making a trip soon but having never visited I couldn't really see myself wanting to live in an area like Des Moines.