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Personal opinion: Chamber. That's what I do with a 1911, Beretta, or Glock. I agree completely with the others here who preach that an un-chambered weapon takes longer to get into action...

That said, I understand your misgivings about carrying with one in the pipe with no external safety. To carry chambered safely, your holster MUST cover the trigger guard completely. Frankly, if you're not comfortable carrying chambered, then I'd rather see you carrying and handling a gun you're comfortable with and in a condition you're comfortable with, than not carrying one at all...

I would also recommend attending one of the many weekly/monthly club-level competitive matches (IDPA, USPSA, IPSC, GSSF, or the like) to get an opportunity to talk first-hand with like-minded individuals and see some of the carry techniques and equipment out there.

Matches are also good for your confidence and shooting/gun-handling skills, especially given that you'll be doing it in a friendly controlled environment.

Personally, until I had been shooting a 1911 in IDPA matches for a little while, I wasn't really comfortable with cocked-and-locked carry myself.