I've always been fascinated with building wealth and generating passive income, but I can't seem settle with one thing and run with it.

I'd come up with all your own assumptions to generate a purchase price. get it under contract, then confirm (via Ptax statements as noted below), your assumptions, if something is off, thats reason to kill the deal.This shouldn't cause so much headache for you, just fire off the NOI and see what happens.

Furthermore, there will be about $20,000,000 in home sales, generating well over $1,000,000 in fees.

If it’s an actual agricultural property and the buyer goes through Ag credit, expect more like 65% ltv (so 35% down payment).If it’s truly a business, market it as such and the price should be based on the cashflow it generates.

From a strategic perspective I am looking to buy and hold multifamily and generate good cash flow ( beating the market in terms of COC return).

One thought I had was if the STR works out maybe some of those repeat customers could rent a "locker" of some sort full time to store their area specific toys/gear.     

I’ve had an insane amount of issues with these guys regarding their customers parking on my driveway.

Aside from that, I think you will find it hard to continually generate losses like you envision.  

My customer has roughly 1.2M equity in multifamily rentals, and his only debt is an 80k HELOC on his 190k primary residence. 

You could have the system inspected and use a generator for power.