What To Do, What To Do....

I'm in a bit of a pickle. A bit of a conundrum, as it were. I'm not sure what to do here. For the past two years, as a family, we've been enjoying skiing. Ok, when I say enjoying, I guess I mean three out of four of us. Apparently, L doesn't like it. 
Last year, he protested going quite a bit. But once we would get there, he didn't seem to mind too much. 
Much. 
I still felt we were dragging him along. And this bothers me. I really want him to like it, to enjoy it with us. I need for him to like it, since its something we can do as a family, and it really helps the long winter go by faster when you have something fun to do on the weekends, instead of staying home and staring at the same walls all the time. 
And here lies the problem - L is perfectly happy to stare at the same walls all the time. So is R, but he does like skiing. I swear, both of my kids would easily turn into hermits if I let them. And I'm a home-body too, but even I get cabin fever during the dismal winters we have here. 
So I'm not really sure how much of L's dislike for skiing is spurred on by his dislike for leaving the house,or if he truly doesn't like the sport. He's like that with every activity he's tried: gymnastics, swimming, art class, t-ball, soccer, etc. He just can't be bothered to leave the house. It's also a huge reason why he hates going to school. Because its not home. (But that's not the only reason.) 
So here is my dilemma - we are in a very tight financial situation now. In all honesty, I really shouldn't even be considering skiing this year; it's an expensive sport as I'm sure you know. But I can also honestly say that before we began skiing as a family, I would feel depressed in the winter. The whole SAD thing did, and still does, get to me. When you compound that with stresses about money and other things, it's not great. I don't want to feel that way. Having this to look forward to really does help. And while I don't want to incur more debt on ourselves, I think it's worth it to save my sanity a bit. 
The thing is, is that I have a small window to save money in respect to this sport. The kids annually need new(ish) larger equipment, which I can get at the ski swaps held in October, and the ski resorts often offer discounts on passes and such if you buy early, usually before November. 
I talked to L last night, and asked him if he'd mind if R and I went skiing without him. He said he didn't care, indicating as long as it wasn't during school hours (that pretty much never happens due to work!), which made me think that he really doesn't hate skiing as much as he says if he's willing to go to get out of school. But he did express to me his desire to have more family time. I tried to get him to  give me some of his ideas of what family time means to him, but that's another post. 
So do I :

1. Get him and his brother the equipment they need anyway,and continue to drag him along, hoping he'll get over it and start enjoying it? **I need to mention here that at the end of the season last year, he ended up falling on the last run of the day and spraining his thumb, so he's probably also scared to ski again, and therefore leads to the whole "Get right back on the horse" adage.
2. Get R what he needs, passes just for the two of us and only take R when we want to go, leave L with Daddy, also hoping next year he'll change his mind? This means that if he does change his mind in say, Feb he's SOL because he won't have equipment. Then I'll feel badly about leaving him behind.
3. Give up on skiing altogether for this year and concentrate on trying to be more frugal, risking SAD? 

Thoughts anyone? I'd love to hear them.