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?

Having the right manager in small towns is challenging

G'Day Alejandro,As a few have already mentioned, take a peak at Toledo also.In my opinion lower potential for long term appreciation but solid/"boring" cashflow.I prefer my portfolio to be "boring" but cashflowing lolLow entry points (Sub $100,000), high rents (Above the 1% rule).Blue collar working class decent folks that will stay and pay.Depending on the area but no derelict homes, yards well kept, cars with wheels and all tenants are employed.Plus, all are sophisticated enough to pay rent online so property management doesn't have to collect rents with bullet proof vests and shot guns lolI'm bias toward Toledo but it's worth considering.Wishing you much success

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.

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).

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.

Take a hard look at your time management.

Managing units is work.  

Section 8 and multifamily aren't for the faint of heart and can be challenging for novice investors both in managing and reselling.

It also includes managing your existing investment well to ensure you aren't bleeding money due to bad tenants, excess maintenance, etc.