The current owner is about 97 and cannot remember what the situation was. 

Is there a better option people would suggest given the situation at a high level?

You'll just need to find the balance of giving amazing and caring customer service to those sellers in need along with remembering as an investor, you are a business and you will need to create a win win situation for both you and the seller.

Everyone's situation is different so it really depends on an individuals situation.RE depreciation: Under recent tax changes ALMOST everything is deductible in the year its paid.

.- 3-4 units still puts you in the residential category- 5 or more units is commercial residential and most lenders will expect you to have experience and will generally have more restrictions on the lending process- A 10+ cap rate in the Boston area will be extremely challenging to find unless you are planning on a massive value add or redevelopment- No idea what your personal financial situation, but a 3 family in Worcester versus a 20 unit requires a very different upfront financial commitment.

Hypothetical situation.

Shoot me more info on your situation and I can help with a recommendation. 

I am wondering if it would be possible to use a VA Loan (no money down) to refinance out of a private money situation?

My question is for those who may have previously been, or currently are in a similar situation.

@Michael Hooper this publication of mine here on BP may help you get a better idea of how to handle these lending situations in the future.