Richard -- as Silver or Gold Elite on CO the last couple of years, and almost always flying on straight Y tickets, I can tell you that when I'm organized three or more days in advance, my upgrade batting average is almost 100%. No coupons, no slips of paper to save, no nothing. And when you're Gold and buy a "Y" ticket you're almost always boosted into F automatically. I really appreciate CO's no-fuss, no-paper, no-limit approach to upgrades.
Where I haven't succeeded is when I've flown on very short notice -- same-day or 24-hour -- or changed my booking at the last minute. I've had very little luck with gate upgrades, whether I've been Silver or Gold.
I think CO's staff, food, amenities and overall attitude beat AA hands down... but on the aircraft front, CO -- like AA -- is sneaking more NG 737s onto transcon routes. (Upgrade hounds beware... we're tussling over 12 or 14 F seats on a NG '37, versus 24 on a 757. Hurts our odds.)
On balance I am proud to recommend CO to be your primary airline! But with your travel patterns, I can't swear that you'll end up in the front seats any more than you do now.