I haven't been to Tahoe in my Tesla, but I did drive across Kansas and up the Rockies in Colorado in Jan/Feb a couple years ago. There's a pretty big cold weather hit - maybe 10%. I've not attached anything outside my vehicle, but I've seen reports that roof racks are around another 10%. A hitch rack might be a little less. Climbing the hill will be another hit to range.
But if you charge to 90%+ in Placerville you should be able to arrive at the resort with more than 40%, according to ABRP. It also claims you'd only use about 20% coming back down.
I'd try to select a resort that has EV charging. Sierra appears to have two Tesla, and Kirkwood has four J1772. Being able to top up once or twice while you're there would be very nerve calming. Keep in mind every other EV is having the same concern so please move your vehicle if you aren't actively charging.
As for winter driving conditions in a Model Y, I was pleasantly surprised. There were only a handful of occasions during my month in Colorado that I dealt with inclement roads, but I didn't experience any excessive performance problems. The car was planted, the power was good, any slippage was quickly controlled. Smooth controls are very important. I did not use chains, but Tesla does sell them.
https://shop.tesla.com/product/model-y-19_20_-snow-chains . When I used chains on my Jeep it was otherworldly.
I look forward to reading reports from people who have made that journey - I'm sure there are quite a few.