I currently manage a long term rental and working on a single family home fixer (will probably convert to rental in the future) in Cali.

I follow the letter of the law( no matter how much I may not like it) that's part of my risk management and my reputation.

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?

Typically corporate/bank owned homes are managed by an asset management company.

I have a few rentals with section 8, and they are professionally managed.

One reason was the condo management company wasn't doing a great job and there were always extra levies. 

Reach out to Lisa Loesel at Short & Suite Management here in Milwaukee. 

The key is building a reliable local team—property managers, realtors, and contractors you trust.

Managing a rental (even if it cash flows) comes with responsibilities, and it might not be worth it for $300 a month.

As someone who occasionally works with these investors, I always try to emphasize the challenges that come with real estate like managing renovations, dealing with tenants, and navigating market fluctuations.