I usually don't mind the wait for my bags when I get home to ORD - it gives me a chance to freshen up, call for my taxi, etc. But on the trip out, especially on a business trip, I am completely unconvinced that my bag checked at the front desk will make it to the same destination as I do.

I'm often carrying 3-4 days of dress clothes, and I'm not the easiest size in the world to fit on short notice (54 XL jacket) if AA loses my suits. But, I know my garment bag is a little over the regs at that point.

I never have a problem, though, because
I understand the concept of gate-checking my garment bag before boarding even begins. I walk to the gate about 10 minutes before boarding starts, and ask the gate agent how full the flight is. If it's empty, I carry the bag on - there'll be enough space. If it's 2/3 full or more, I ask to gate check my bag right then and there. I always get a friendly response from the agent, becuase (s)he realizes that I'm trying to save everybody as much hassle as possible. I've never lost a gate-checked bag - where could it possibly go??

The key, though, is to ask for the gate-check before the agent starts boarding. Otherwise, I think that you are seriously inconveniencing the gate agent, the FAs, and your other passengers.