My wheelehouse is long term management of investment properties, but I do have a good relationship with a loca Chattanooga broker who helps investors in the area.

Do managers that advertise 8% only do 8% when there's a bundle of doors to manage?

Wholesaler that I managed his airbnb.

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?

with some commercial brokers, property management  any expert help is an advantage !

Having the right manager in small towns is challenging

If you can find an investment that pays for itself, you won't be so nervous about investing.I also recommend you educate yourself on how to manage well.

And at the top, you need three key people: an artist (to deliver a great product), a manager (to keep things running smoothly), and an entrepreneur (to drive it forward).

Take a hard look at your time management.

He usually buys in C neighborhoods and has to do heavy rehab, but he's a construction guy that also runs his own property management company, so it's 2nd nature for him.