I live in an area that has a vacancy rate of 0.8%, our homes have increased in value 40% over the past ten years, We have been voted numerous times top city to live in NY.

I've been in contract to purchase a single family home for almost 2 years (numerous extensions).

If your gambling on appreciation, that's a pretty safe bet.

That might mean moving to a new area/state where jobs are numerous.

If I had numerous STRs, I would be looking for a way to automate the PIN establishment with the guest.

It looks like crime is higher in this neighborhood, but is mentioned as being one of the best sub-markets for investors in numerous articles.

You also would have numerous options that I would be happy to help you explore more, when it comes to how you structure the deal.

First off I know this is a very subjective question based on your area and personal goals in real-estate.My market is Colorado.I was spoiled before values increased and with a 2.6 interest rate and my first rental cash flows $600/m and is a townhome.I’m looking at numerous opportunities that after all expenses including cap ex, vacancy, and repairs cash flow $150-250 per month with not a ton of opportunity to increase rents for the time being.

That's a bit of a gamble for the landlord and it means you price your property higher which may draw less interest from someone browsing listings.  

Pertaining to the Repairs, this has happened numerous times Security deposit that was meant for the tenants.Tenants lease is current