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?

Quote from @Carson Hyland: Even if you buy the right property, failing to manage it well will kill your cash flow. 

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

I am based in Virginia and licensing requirements here seem manageable.

We run into this especially at out parcels in grocery anchored centers, and our users generally can't make a ground lease work for the business case so the next best thing does tend to be the BTS or we often do Reverse BTS deals where the majority of the building design and management etc is done by the tenant. 

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.

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

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.

Practical Tips for Managing PropertiesFinding Good Tenants: Screen thoroughly.