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.

Or worse case in the S&P 500 (all a gamble I know)3) If I keep it, buy another home then I guess I can sell it in 2-3 years and not pay capital gains on the appreciation but if I make say $175 a month cash flow (after PIPI, 6% maintenance, 9% vacancy, no management as I would manage it while I was local) in 3 years the roof (partially) will for sure have to be considered a sellers concessions which would remove a chunk of that equity/cash flow I just built up but if the home goes up in value that could negate that.Current monthly is $1650 (that includes HOA) - Would rent for 2500Taxes are low (based off 215k purchase price) but im guessing if I convert it to an investment property and remove the homestead it will jump up to the new appraised level?

I'm taking the gamble that I can finish the 6th unit and get the zoning modified somehow to further increase casflow.

They just change the subject and the latest story is that, "We took a gamble and it didn't work".

Versus doing one large building, don't want to take the gamble, thus we will stage smaller buildings as they fill up.All units will at least have one 12 wide x 14 tall (clear height) panel door; 16 foot eaves.