I'm trying to decide whether I should stick to three cheaper, single family homes (long term rentals) or one expensive vacation home for short term rentals.

Vacation rentals in NYS have always seemed a bit risky to me.

Why not let me try this real estate thing to try and speed up the retirement part of this or get us some extra money coming in for vacations or however you want to frame it.

Bought a 4-Unit ($520K), gut renovated with my cash, fully occupied, furnished vacation/short-term rentals (with a waiting list).  

My husband and I are full time vacation rental investors.

I would buy a set of bolt cutters, take vacation tomorrow, and hop on a plane. 

My next door neighbor has a STR in a prime vacation market.

My water bills are coming in higher than I anticipated, so I'm toying with the idea of installing submeters in my units as tenants vacate and turnover.

Tenant A legally (or illegally) vacates, leaving occupant B behind in possession of the unit. 

Took a nice long vacation after becoming kid-free and house-free and now looking for my next home somewhere warmer, drier, and ridiculously affordable in comparison to Seattle, WA.I've been reading the forums here for months trying to learn as much as possible about finding a deal that fits me.