Leave the gambling to the habitual losers.

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.

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?

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

https://www.wlky.com/article/k...Kentucky has fallen behind peer states in gambling and marijuana missing out on millions in revenue, hopefully we can speed this up and boost Kentucky's economy. 

With the lawyers I've spoken to, seems like this is a 6-8+ months process.Is it worth it to take the gamble and hope that the tenants will just take the money and go, as this is too good of a deal to pass up (even with the 50/50 chance that I might not gain posession for another year)?

There was a Starbucks being built next door so took a gamble.

Appreciation is speculative, much like gambling.