I want to know more about the area and build a team that can help me purchase and manage properties.   

Just make sure the management part is taken care of.

@Jason Brown - I'm a CT based investor, flipper, and property management company owner.  

My landlords use Azibo for management and RentSpree for screening, but there are a million options.

Long term rentals are easier to manage and come with less risk.

Do you think purchasing a property in Philadelphia, PA, and managing it remotely from Westchester, NY (Roughly 2-2.5 hours away) with the help of a local handyman would be too much of a stretch?

If you ever need help running numbers or managing your property. 

Getting a rental license as an out-of-state investor is doable, but you’ll need to manage inspections and compliance.

If you're in it for the long run you'll learn that management makes a good investment into a great investment.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases.