I was in your position 12 years ago when I relocated to CO from Michigan. I caught the elk bug bad, and still have the disease!!
Sounds like you're already convinced on using an outfitter, which is the correct way to go. You may want to check out Dean Billington of Bull Basin Outfitters (Kremlin,CO). I did my first elk hunt with him and was very happy. He has access to some very large ranches in very good elk country.
If you want to do a cow elk hunt, look at Kiowa Outfitters in Raton, NM. The owner, Tim Barclough, is former NM Fish & Game. I've hunted a lot with him. He does his cow elk hunts on the Vermejo Ranch which is owned by Ted Turner. Big and very healthy elk population. Pretty much 100% success rate for late season cow elk. Whenever I didn't get a bull elk in CO, I'd go down to NM and cow elk hunt with Tim.
Your 30-06 will work great for your hunt, so use it. Honestly, you can never have too much firepower, so use the 338 if you shoot it well.
Feel free to PM if you have any other questions. Good luck
Doug
