It is currently a 2/1, we plan to convert to a 3/1.

We also considered converting the garage into a 3rd bedroom to add value through live-able square footage but aren't sure how far we should go with it before we start looking into a cash out Refinance.

(large garage to convert into a unit, converted a shed, basement that you've subdivided into two units, adding a bedroom, etc.). 

The better route is to convert to MTM with 45-day Notice Period, otherwise you get to charge an Early Termination Fee. 

Took a few years to get licensing, permits, etc, to either restore it to being an assisted living facility, or convert it into one.

If you buy the "on sale" office building, it will cost some money to convert, but if the savings is there on the initial buy price to more than make up for it...And then let's say 5 or 10 years from now the "work from home" fad is over and offices are in demand again.

Mean sea level averaged across the entire world is around 2 mm/year, or 6-8 inches/100 years. 

In one case I converted the detached garage of a SFH into a legal ADU essentially converting it into a duplex.

we currently live in long island, and was thinking of upstate NY, as that would be a drive away, if we ever decide to convert the STR to our vacation home.

Cash flow is mostly a myth and it's all about appreciation unless you convert them to mortgage notes or CFDs but then you lose appreciation.