Also, for those who invest OOS, do you find one market you specialize in or do you tend to bounce around and cherry pick from markets in several locations? 

I can say I'm biased because I'm located here, but the numbers work and it meets all your conditions.

Given the location and how the town has been developing it seems like a good investment opportunity for rentals.

Many experienced investors are humming a long similar to prior to the rate hikes.  

However, not one general location is going to help you determine whether it's a good market for multi family or single family etc.The one true way to start looking into a market is talking to an agent who knows the area.

Was able to gain some leverage prior to negotiating which resulting in a great outcome What was the outcome?

Quote from @Rachel Jane: First post, no idea what I’m doing, lolMy grandfather passed away and left me his condo, which is fully paid off (and located in a seniors residence) It’s worth approx $500,000 (CAD).

Given the property is located in the Poconos and the property is vacant more regularly as an STR there are proactive measures  you should  be taking such as making sure there are heating sources so that the plumbing does not freeze and ensuring there are no blocks in the plumbing lines with routine checks.

Personally I like the Section 8 program when the property is located in a super poor area with a ton of blight and crime.

Portsmouth, known for its historic charm, offers higher prices but strong demand for both multifamily properties and short-term rentals, with premium rental rates for well-located properties.