It can be done and the job market there (high military/health care/maritime industry components) support a transient population and solid rents.

Drugs - Health Hazard, are reasons for evictions, but not much else.

Checked health-Aids (I was negative) criminal background, credit history, education, work history, skills, income tax etc.

Also ask the County Health Dept if Sewer is available or if you'll need Septic Systems.That will get you started.

My first house I just closed on the middle on the month is directly across the street too :) the only reason why I asked was because the Boston Area like a nice place to move too.

As mentioned above, you have multiple options to consider but the 3 main ones are HELCO, cash ur refi, sell and trade up via 1031.before going down that road you will want to take a deep dive into your current properties health.

Due to her health and age we are considering to let her move in with us and convert her property into a rental.  

The premise is this: having a large number of clients who add little value hurts your productivity and mental health (now matter how much collective revenue they are bringing in).

Reserve pension is still better than no pension and you would still get base access and health insurance benefits.

But when you're going to brokers as a 'value add' buyer, and go and inspect the building with a fine tooth comb for errors, you're not REALLY a value add  buyer)