@Wayne BrooksThanks Wayne it gives pretty good insight, it was a single family home but the previous people converted it into 2 family home because it was quite big could have easily be converted into 2 family legally but somehow they did not chose to and we bought it on auction, county court auction.

I look for properties that I can easily house hack by being able to convert the existing spaces (spare family/living room and garage) to an ADU and then rental it out. 

I'm split between "converting" into 2 retail spaces, or an office building.Option 1: Divide the building into 2 retail storefronts, one approximately 1,500 sqft, and other 1,200 sqft.

With a strategy like yours, it would be very advantageous to own a casa do pueblo, which would allow you to build-out additional bedrooms, bathrooms, create horizontal divisions, maybe even convert a local into... another apartment, etc.

To answer the question it appears you are asking, yes you can convert/refinance a VA loan guarantee to conventional financing. 

Potential to convert basement to a third unit.

I would say to find a realtor who works with investors in the North end to nail down those numbers, honestly I would be inclined to convert the single car garages into a 2nd bedroom. 

@Charlie Shew Have you ever looked into converting your rollover 401k to a self-directed IRA and investing in real estate syndications?

I have had a number of homes 3000 sqft plus that could be converted/ used.

We had to convert away from STR in the off season on the one unit that was STR year round so its cash flow was reduced a little.