I have five houses in Memphis area, and the biggest problem has been finding a good property management company. 

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

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

Are you currently self-managing or do you have a management company?

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.

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

I would try and manage it yourself if you have the time and effort. 

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?

I have been following the Real Estate Investing industry for a while and just recently decided to put my focus into it and implement a plan I had in mind for years.So I went down to Puerto Vallarta I put together a team of local realtors, brokers, contractors, property managers and a lawyer. 

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