@Richie Thomas My lender says they don't require PMI since they're a portfolio lender. I never thought to second guess it, but I do remember asking the question a few times. Looks like it was built 1963, but you're right the homes in this area definitely skew to be a bit older. I haven't calculated any repairs since I figured I could get any repairs done myself while living there, of course I see that still leaves me without calculating cost of materials.
The $6 a month for insurance is definitely wrong in the calculations - realistically I'm looking at $80-$100 a month for homeowners insurance. I hadn't really considered STR either - depending on what I can do with the attic, that could be a great idea!
@Scott Wolf Thanks, I realize there's a bit missing to my calculations, even then it's still not a solid deal right?
I'd love to move into Duthcess County, but I work much closer to Westchester so I have to be mindful of my commute. So far the only Dutchess properties that could make sense are in the Fishkill, Wappingers Falls, Hopewell and Pawling areas - and then I'm hard-pressed to find what I'm looking for. Although, my only source of leads is through the MLS.