Go with JC/enchanting. Especially jewelcrafting because it allows you to mix and match the stats a lot more since you get 3 gems. The other professions that have one big enhancement for one item usually only give you 1 or 2 options so if you later decide that you wanted... say +35 spell penetration or something, can't do it.

With prices on my AH it cost about 3500g to my main to 405 JC. It was the low levels that killed me, and certain ranges like 250-275 cost me probably 1000g. Yeah, it could be done for cheaper if I'd checked the AH constantly or tried to farm my own stuff, but I considered the value of my time - 1000-1200g in an hour with a 5 man team doing dallies, more if I wanna run a few instances that day. Seemed much more efficient to just get it all done at once rather than spend a week checking prices to save 1000g that I can make in an hour.

Enchanting is nice to do after JC. You will have literally hundreds of items to disenchant between 1-300. This probably equates to 1000g worth of enchanting mats. That's enough to get you about half way to your goal in enchanting as well, for free.