You can do any caston, though I wouldn't recommend the backward loop method. You can co an extra stitch, slip the first stitch, knit around, then knit the extra together with the first st that you slipped. That makes the first round even as well as snug.
sue- knitting heretic
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As far as cast-ons are concerned, I would go for either a long tail cast on or a cable-cast on. Both are stretchy cast ons -- I think the long tail is supposed to be the stretchiest.
Then when you cast on for your hat, cast on an extra stitch and slip it from your right needle to your left needle and the knit the slipped stitch and the first stitch together. That should give you a neater join.
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I have made a lot hats on circular needles and I use a normal long tail cast on most of the time. If for some reason your's are coming out too unyeilding you could cast on with a needle a size or two larger than the one you intend to use.
Another cast on that is suppose to be very flexible is the twisted Norweigian cast on. I think you can find some information about it on someone's blog or somewhere by doing a search. They use it for sock cuffs.
THANK YOU all for your help! It is much appreciated. I definitely have some good ideas now of things to try that I never would have thought of, and most of them are so basic. Learning all the little knitting tricks shared by people with experience(of all levels), that's one of the many things I love about this hobby! Thanks again!