You are essentially gambling that growth in your primary market will spread to the secondary market you invest in. 

I quit cigarettes, I quit gambling, I started making coffee at home, and eventually I became responsible with money.

It has a tenant facing web portal, collects and deposits my rent in 1 day via ACH for no extra charge, offers debit / credit card payments as well for a service fee to the tenant, and SOOO much more.

You're really betting on appreciation, which is a real gamble right now with ridiculously high prices and a good chance inflation is going to worsen.

Can anyone give me any insight on whether buy and hold can still work over the long term, or is it just a gamble?

Check out DealMaker 2022 with Jim Ingersoll via a web search.

Spiders have fangs that inject venom into their prey, and most kinds spin webs in which to capture other insects." 

I started a Philly landlord group to navigate the web of city ordinances, share vendor info, and even advocate a bit for example.

Second, anyone who has a weeks worth of SEO education knows that double listing with conflicting information DESTROYS the web presence because to the underlying systems of the internet, it flags as a scam (same property with different listing contact #'s, posters etc). 

Then they did the downward spiral with addiction and gambling and didn't pay rent.