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.

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

Especially if you are hiring property management.

It sounds like you’ve got a solid foundation with your rental property, and I love the ambition behind your plans to build a property management and maintenance company—it’s a great way to take control of your investments while creating additional opportunities.Best of luck to you! 

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

Quote from @Noah Laker: I'm a local broker and investor, and manage 100+ Airbnb properties for clients.

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

I am a voice of common sense and help them come up with the best way to manage STRs.