The bigger cabins are much rougher as groups - sports teams, schools, church groups, multi-family groups, etc. - tend to damage things. 

You are gambling.

That’s the gamble...

I guess it’s all a gamble really.

At the time, most were for wedding guests and youth sporting events all of which were cancelled.

It looks like there is some low hanging fruit in the summer months and opportunities to build business in the winter for someone who is a go-getter and wants to break into some niche markets that come to the area for winter sports.

While you are bragging about your deal skills, I have shown proof and scaling to $1M/month. still all I see is you in a fancy sports coat next to a fancy car.

I want a linear market because inflation adjusted appreciation is a gamble, no one knows where the markets going.

The key to any of this are the partnerships...with your other GPs, brokers, property management, CPAs, and attorneys...this is very much a team sport, and the best way to play is for all sides to win.

The only way I would consider what you are proposing is if the equity from your coop is enough to place enough of  downpayment (think 50% of purchase price) on a small multifamily (think 3-4 family) so that the income from the new property is enough to cover all expenses of the new property as well as the loan (or a significant percentage thereof) on your personal residence.It's a gamble that can break you or be the beginnings of your real estate portfolio.