Boston is the 3rd most expensive market in the country, and DC is the 4th.

Live in the primary.

I think you would be wise to sell and use the VA loan for your new home. 

Competition with owner-occupants and the age of the homes (70-120+) will squeeze your margins and expose you to a fair amount of risk.

What you can require legally changes depending on your location. - If you make the above clear in the listing, you will immediately get fewer applicants.

Some people like Yardi and some like the next one. 

As I dive into all the different paths I can take (single family vs multi-family, short term vs long term, cash flow vs appreciation, local vs out of state, etc..) my mind is scrambling and I've ended up doing nothing at all.I'm looking to join a mastermind that meets consistently and can really motivate one another to take our businesses to the next level. 

The cheat sheet/example greatly reduced time.

The applicant needs a credit card to complete the process and they charge more than $25.A lot of landlords in Milwaukee do the same. 

The insurance is higher along the coastal areas because of potential hurricanes but not bad the further north you go.