I don't think I'm gonna work when I have a personal golf course that needs to be played on!"

Just playing the game.

Every time you paint this ceiling, the moisture you're adding in the paint causes more of the drywall mud that was used in the texturing to pop, or patches to fail, in different placesAttic condensation and a lack of ventilation may also be playing a role here, but you have to check this first.The way to be sure that this is going on is to get up there with a ladder and spray a section with water in a spray bottle to the point where it's just starting to drip.

I couldn't tell if your plan was to Brrrrr or if this was an intentional value add play, but either way I think you did yourself a favor over the long haul.  

Also, not all condos in NY will allow a down payment of less than 10%.Full disclosure: I am not sure how all of this will play out in NJ when it comes to looking for condos.That being said, I think it takes sense to explore multifamily options in NY or NJ when taking  your dream/goal into consideration. 

If you are thinking of multifamily, as in 5+ units, it is a smaller playing field, and you don't want to burn bridges with realtors by wasting their time because you didn't know something.

Momentum play.

The last couple has more of an appreciation play than cash flow (not in the red, just lower cash on cash return) and we see an escalating rate as time goes on.These are 2 cottages on 1 parcel of land , so they ARE seasonal right now.That being said, my abutting neighbor , who we get along with very well, has decided to put her vacation rental on the market.

Also, play around with the BiggerPockets calculator if you haven't already.

That being said the numbers you provided don't play out as a cash-flow rental if that's the strategy.