Or what is the reason? 

You'll find a lot of hard working contractors.Have something to write on as many of the contractors won't have business cards.You'll still want to screen them a bit because, "there's a reason they work with the hands, not their heads":)

For a variety of reasons, including keeping this potential project "need-to-know" only right now, I want to get a ballpark estimate with full understanding that the goal posts could move in either direction as the project gets more discrete. 

I don’t know what the costs would be to “scale” from the volume you do now to a volume you’re targeting, but it’s probably a reasonable investment.  

It's open for interpretation, but if it went in front of a judge, they would look at the reasonableness of the situation. 

FHA will not use any short term rental data.Something else to think about - any reason why you wouldn't use a Fannie Mae loan here?

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

Hey Milena, have you checked for reasonable comps in the area?

Looks reasonable to me.

(The same reason many people (maybe mostly men?)