If I put off using the VA Loan until it makes sense (perhaps after a correction to the NYC market), my immediate plan would be to find a cash flowing 4-plex in the Mid-West and BRRRR it.

Even if these inflated properties to a mid point of half of their current values wouldn’t it be better to hold the cash, pay 30% gains and redeploy after prices normalize?

We are in our mid-40s, with 4 kids and college costs beginning in two years.  

It looked like it was built in the mid 1800's and only 1 unit was habitable.

My vrbo clients are in their late 40s (in average) while on airbnb the average is closer to mid 30s.Now the interesting part about your observation is the fact that 2 similar units in the exact same location are more or less popular in a platform.

If funds are going into passive deals, then you're probably looking at low/mid-single digits (unless borrower/deal is questionable) which isn't anything to get excited about.Have you considered partnering with somebody who operates and a more favorable market or looking at being a passive investor in syndications?

If you were to use a mid range product I would go with a vinyl plank.

But it's important not to get your heart set on something based on a Discover card statement or Credit Karma if you are anywhere in that mid-range from about 580 to 740 that about ~80% of consumers are in.740+ is the best rates for conventional conforming. 760+ is the best for PMI.

We bought our first two properties this year and are learning more about Baltimore for hopefully a third property early to mid next year.

You simply need to have a strong credit score in the mid-600s, a 20% down payment and be prepared to pay an additional 2pts or slightly more in Lender Costs PLUS closing and realtor costs.