I'm going to Aspen via Denver next week, and I'm on SW nonstop from Wash DC. A regular ski bag with skis+poles and a boot bag (with only the boots inside) counts as 1 bag. My suitcase, up to 50 lbs, counts as the other bag. No fees if I do it that way.....
Of course, I'm not bringing one pair of skis. I'm bringing 2, and 2 sets of poles, and I will probably be bringing 3 pairs total back with me. I have a Dakine double roller bag, and it isn't all that light, either.
So, from what I've read here and on the SW site, I should be prepared to pay $75 for that loaded up double ski bag, but I will do my darndest to make sure that it weighs a hair under 50 lbs. I'm bringing an extra ski bag (just a thin one) in case I need it for the 3rd pair, and if I have to pay an extra/oversize fee for the double ski bag, then so be it. I'll put the third pair in the thin bag, and that will count as one of my 2 that I don't get charged for. The dude I'm travelling with will have 2 pairs, and if we get charged fees, then worst case, we can put our extra pairs in the big bag and pay for only one extra between the two of us.
There is a decent chance, however, that I will not be charged any fees. Load the double bag up to 50 lbs, suitcase just under 50 too, + bootbag all count as 2 bags, fee-free. That's not exactly in line with the rules, but it is what might just happen. Using a skycap might help my odds, too....especially if I'm nice, as a previous post said.
I have a NS flight there, and the same deal back - that's two tries, and I love gambing - as long as I know I'm playing. It's all about expectations. They aren't better odds with any other airline!
To get the three pairs in the double bag, I'm probably going to have to remove bindings from at least one pair. There's always the option of using a priority mail large flat-rate box for $15 to send a couple of pairs of those back to myself. If it gets me under airline weight limits, then it will pay for itself. I bring a digital luggage scale for these sorts of endeavors, btw.