When should I submit Timberline application?

I know nothing about resort hiring so take this with a grain of salt, but my guess is yeah its too early because they'll all be focused on right now and not next season yet. Could always just apply twice

Years and years and years ago, I applied about this early. I can't remember what I was told right after I applied. It was either no answer, or check back with us later. I did get a call around April with them wanting to either give me the job or interview, but I had already secured a more lucrative job in line with my career path and told them to disregard my application.

It shouldn't hurt to apply now. Just make your application very clear and indicate that you are excited to work hard as part of a team, and you should be fine. Make sure to follow up if you don't hear back. Fine out who is in charge of hiring and try to contact them directly. Offer to do a Skype interview. After any interview (phone, Skype, or in person) at the very least write a genuine thank you email.