In Jackson, everything is an adventure, including traveling TO the airport. The other day I had to stop and wait for a herd of buffalo to cross the highway, no joke.
Early flights always offer a better chance of having you and your ski bag end up where you intended at least by the end of the day, but there's no guarantee. Prepare for an adventure and if you happen to have a smooth day, consider yourself lucky.
Get a credit card that waives baggage fees.
Take good care of your friends now, so you can ask for favors later.
Some of the hardest places to get to are the best—that's why the snow stays good!
The only trick that seems to work is not caring weather you make it at a desired time with or without baggage. Letting go and being willing to take the ride seems to be the only way to beat the suffering of traveling.