Welcome to FlyerTalk.

I would focus on your last bullet point. Wait until 330 days and then start checking some dates. Hopefully, you can be flexible with the time you would like to travel. If you are, I think you will have success getting the tickets you want at the 35,000 mile level. Also, if you are an Elite, that might help as well.

When planning a trip to HI in 2003, I didn't even think of using miles at first. I just figured it wasn't possible unless I wanted to use EasyPass (which I didn't have enough for at the time anyway). However, I was able to find standard award tickets for the dates I wanted.... and only 5 months out. I didn't start checking until mid-December for a trip in the beginning of May.

Also, don't forget about Delta and Northwest. If you can't find CO tickets online, start calling and have an agent check those flights for you (NW should come up online but not Delta I think).

Good luck.