Jakerado,
Based on the numbers my guess would be you live in the Bay Area, if not my ideas below can probably be applied elsewhere (west of Denver). If you are on the East coast, option one below would be the most realistic. Is it imperative that you have a place that guests can crash at and entertain or are are you averse to camping or sleeping in a car/van? If I am wrong on the Bay Area, I imagine you can find similar alternatives if you do a little digging, so think of my ideas generally too.
I lived in SF for a while and would do the drive to Tahoe every other weekend. One thing to think about owning in the mountains is that if you are near the resort there are probably going to be HOA fees involved and if there aren't you are going to have to worry about paying for plowing and related costs since you aren't there to take care of it yourself and will be skiing when you could be doing maintenance. I had my season Pass at Kirkwood. Talking to a guy on the lift, he bought his 1 BR condo across from the lift for about $100k 20 years ago. I believe his mortgage was about $400 but his HOA and heating put him at nearly $1,100 a month. Even if you don't have HOA fees, you gotta account for $30-$60 every time you get plowed out and heating (at 55-60 degrees when you aren't there).
In terms of your in-city costs, is there a place you could park a little farther away to reduce your in city costs. Maybe rent the car (if you bought one) on Relay Rides during the week to cover costs. If you park it at the airport and do Relay Rides you may not even have to pay for parking (i think the car has to have <100k or 75k miles for relay rides)...
Here are a few options I did or thought about:
1) Join a ski lease, even if through craigslist - maybe $1500 to $3000 a season for a bed or room, but you are just paying for the season and will likely have people to ride back and forth with regularly. The fuel can be expensive and driving that much (and your parking) so it would be nice to split that cost and maybe not have to buy a car. I would have considered this but I had a Kirkwood/Heavenly pass and my friends had Squaw Passes. I wasn't gonna wait in lines and pay twice the amount for the pass.
1A) Buy a place and rent it out as a ski lease/vacation rental and that could cover your costs... This could be a great option. maybe you could even make money... I could have considered a ski lease in South Lake but that didn't occur to me until I found a cheaper option...
2) Have you heard of the Sno-Parks? They are managed parking areas every 10 miles or so around the Tahoe area in the national forest to provide back country access. There is one 3 miles from kirkwood and if you can beat the storm there that you know might close the roads coming in you can get the whole resort to yourself... There are also sno-parks on the way to South Lake and North Lake. It is $5 a night to park and there are bathrooms. I got a 0 degree down bag at the REI garage sale ($30), I would pitch my tent before sundown, 50-100 yards in out of site. Head back to the Kirkwood Inn for a giant bowl of chili, hydrate, fill my nalgene with hot water to put at my feet and go to sleep in my ski gear (maybe throwon a puffy coat to make sure I am cozy.) there are some more details which, if this is something that interest you, I can fill you in on if you like. You should do research b/c you need to make sure you are prepared for winter camping, it can be dangerous if you are not set up properly. But it can be awesome.
I imagine this isn't just limited to the Sierra's either. You can camp pretty much anywhere in the national forests (where most ski resorts are) as long as you can park legally. If you get a car for this, you could do a ride share through one of the websites b/c people are always looking for rides to resort areas. Also, I bet you could create/find a meetup group to do the winter camping or ski-lease with. There are all kinds of cool groups on meetup - some people can be 'different' but there are also people who are looking for others that share their passion.
2B) If you buy a car, buy one you can sleep in. A wagon or maybe a minivan (or pimp out cargo/mini van and make it a small camper) and park at the sno-parks or walmart if you can stomach trading the wilderness for all night street lamps (A lot of resorts don't allow overnight parking). But keep in mind fuel cost on the 360 mile round trip and spread that cost to other riders.
If you decided to do the camping/car camping option, you can still get a hotel room on nights you are with friends or want a more civilized experience. However, if that isn't your cup of tea, I think some mix of a ski-lease and rideshare could be the way to go, but there are the maintenance considerations ooeei mentioned, so being the leaser mitigates those concerns if it is not something you want to deal with However, if you approach a winter ski lease/rental property with an open mind you might be able to make money in that scenario and have creature comforts. Enjoy the snow.