To keep it short, just from knowing him as a friend and knowing the level of success he has, I already trust him enough to put money into his projects, but I know I should be responsible and do my due dilligence.Essentially, a big project right now is a cabin in a very busy vacation spot that is going to be about $2m.

That is a vacation rental that my family and I use for a few weeks out of the year so it is not strictly investment.

(Max vacated rents - your monthly mortgage payment) = +/- net cashflow.

2) What would happen if someone used the above steps, and instead of transitioning to an MTR, they got out of the rental gamer and turned their property into a vacation home?

The most common benefits a landlord can get from an arbitrage agreement are: reduced vacancy expense, decreased maintenance costs (most arbitragers agree to fix any damage done by guests), increased rent (most pay a premium), reduced number of hours managing the property (aka it's more passive)Some less common benefits, but still worth mentioning: Using the property to host their own guests at a lower rate during the "vacation season", Revenue sharing, arbitrage managing landscaping, and other management tasks. 

Evolve Vacation Rental:Evolve is known for being hands-on with STRs, providing everything from marketing to booking management, guest communications, and cleaning coordination.

In both notices, they alleged that they served you with the respective document at (the address you provided the court in the Summons.)While the Clerk clearly accepted these documents, I see no record of any proof of service/certificate of mailing entered into the case for them.The only other thing - the last item - I see is, another week later, DEFENDANT’S EMERGENCY MOTION TO VACATE THE FINAL JUDGMENT AND WRIT OF POSSESSION, which, to me, reads like a poor attempt to show their client that they did something (from what I can tell, the allegation that the tenant vacated a week before you obtained the final judgement should be the grounds to justify vacating the judgment now.)The Court said nothing to either of these 3 filings by the law firm - according to the public records I see.Seems like the horse was out of the barn when that LLC (the law firm) entered the case, but, again, I am not a lawyer.

I purchased my primary residence and a vacation home in the last five years, working with a great buyers agent. 

Instead of figuring out the technology requirements, how about flying to Denver for a nice interview and vacation that's also a tax write-off?  

There wasn't a firm decision that he made at that point in time, hence things were undecided and unsettled. and not at any point in time, Tenant sent a written letter of move out intent/notice until recently, mid-August '24, when I got the first written "move out notice" from him via "email" that he ll vacate the house on Sept 01 and that the payment will be left on the counter.