I agree with the closer to the metro the more expensive a property is, but also provides more opportunity.  

Most 3BR turnkey homes are closer to $285K and upwards, so with money more expensive, and minimum rent of $1800... possible break even scenario.

However, price points closer to 200k-300k.

@Camille Romerounless you are able to spend some significant time in your chosen location in person, and work on building a network there, i would pick a market closer to NYC, within a couple hours.  

Regardless if it was for tall grass, unlicensed vehicles, leaving the trash out too long, malicious animals, failure to keep snow removed from path to mailbox etc. 

I can't tell the future, I just will tell you markets behave when supply and demand are close(r) to be met.

Here are a few ideas to explore that might help you get closer to homeownership in San Diego without selling:Cash-Out Refinance:Refinancing one or both of your El Centro properties could free up additional cash for a down payment without selling.

Are you buying amazing deals or are they closer to market value?  

Dundalk I would prefer compared to Essex as it's closer to the city. 

I understand Vermont has slightly more stringent regulations to contend with but it would also be closer for us geographically and thus potentially easier to manage.