However, I live close-by (30 minute drive), recently retired from my day-job, and if the loan is not too large, I might be willing to do a deal just to learn a bit more about another side of RE.  

You'll need to really look at yourself and understand what you do well and enjoy, at the end of the day if you enjoy what you do you'll have more drive be successful everyday. 

How many weekends do you want to drive up north to find, purchase, setup and maintain an STR?

Driving a car is legal, as long as you follow the rules.

Out of state investing in cities within a reasonable driving distance may be a good option. 

An in-house attorney would focus on resolving issues efficiently rather than driving up fees with extra billable hours, which can happen with outside firms.That said, I’m questioning whether this is the best perspective.

If there are any community members that are local to Westchester County or the surrounding area and have time to meet up and share experiences and tips, or even have projects themselves that I could provide some help within exchange for the guidance please let me know!

I have a close friend who constantly drives up to the white mountains so can definitely understand the draw.

Do you see Nike cold calling customers or driving for dollars?

Of course they are going to have bad credit or they would be looking in a better area.Another thing you may want to consider to drive more applications is to not charge the application fee.