I have a close friend fighting to get their $20,000 EMD back from New Western on a deal that went sour.

That’s not exactly an unbiased opinion.In my opinion (not a cpa, have no fight in this) you paid way to much.

I think it's a fun idea that will leave a bunch of owners unhappy, fighting over the weeks that they want, and owning a very illiquid asset...the buyer pool for 1/8 ownership of a property in Wisconsin is pretty limited. 

No property owner should fight you on any of these requirements.

Unemployment is DEVASTATING to men, and that 18-35 year old segment are the "fighting age" men that could cause said revolution.Given our history (this country was founded on a revolution) and our 2nd Amendment, I think that without a job to keep them fed this surely a likely outcome without UBI or some other sort of measure to keep them pacified. 

But consider this: if an alcoholic was sobering up and not feeling well as a result, would you give him a round of shots to make him feel better in the immediate or encourage him to fight the feelings of withdrawal and enter treatment?

So, you lost a little on the first month or two and then you lose the whole month when they begin to squat with endless excuses and fighting and lost sleep for you.

I like knowing that my insurer will be in any legal fight (the first $10M of loss is on them). 

Technically speaking, a cost seg is moving from an “impermissible to permissible method of accounting”, so you could argue everyone must (but the IRS wouldnt fight you on this haha)You should get a free ROI analysis then run it by your tax advisor

@Cullen EckertYour legal reference while being a nice try is really invalid because the court overturned it because governing docs did not include it whereas if it is a deed restriction that is completely different from that caseIt doesn’t mean you will win or lose but be prepared for a hefty legal fight that could cost you tens of thousands to defend and the HOA going to make your life.