Sky lodge rentals don't do as well during low-snow seasons in the Berkshires.

I ran the numbers with the latest interest rate and removed the common area cleaning & snow removal cost as i live in Minot. 

I live and invest in Milwaukee, Wisconsin and the winters here can get pretty cold and some years a lot of snow.

Winters are milder than western Pa. and no lake effect snow. 

Snow, rain, heat, sick, ... dude...

There's probably a lot more people looking to buy & move in the last 3 months when, by the time of close it won't be snowing & the in laws won't want to come over, the kids won't need presents..

Last winter, with the early and often snow, occupancy was fantastic - following several years of sporadic snow and occupancy. 

How about  accounting, legal, lease up fees, snow removal, Pest management, or CapEx reserves?  

Reason being you only have 2 units over which to spread all the fixed costs, like lawn care, snow removal, etc.

This is anecdotal from my end looking at vacation properties in a couple of ski/snow markets and a couple of (non-San Diego) beach markets.