@Ryan Sommer
I have been on the moutain, with rentals since 1997. Before Airbnb was an online model. The great thing is Big Bear has been set up for owners to rent their homes for years. Get a permit, follow the rules and everyone is happy. Recently more rules have been put in place to make it challenging for Airbnb to make any money and or discourage vacation rentals all together. The biggest reason for this, the people actually living on the moutain are being forced out by high priced sales of their month to month rentals, over saturation of vacation rentals. I can get 100 applications for a month to month rental right now.
The other thing to think about, if your paying top dollar you’ll have to charge top dollar. Before Covid my yearly average was around 167 nights a year (self managed) maybe a 10yr average. But while I was building a clientele I was at 122 nights for years.
Basically if you Ski, love the snow, hiking, getting away ect, it will be worth the bucks you spend out of pocket during off season or between rentals.
Good luck you have to start somewhere…