It doesn't help that the economy(s) are so massively over-inflated, and that is literally half the problem IMO. Quest gear only nets you so much before players are encouraged to use the AH, but 100g+ for a level 15 green bear sword is ridiculous for most people starting out. My first caster ran with a white cane whose only stat was the one I had enchanted onto it for at least 20 levels because I literally couldn't afford the stratospheric prices on the AH. Playing these servers takes an entirely different mindset than retail.
Since I doubt you're going to get any love here, some tips--
Be self-sufficient. I know you want to min/max, but unless you are part of a guild or have wealthy friends, you won't be able to front the money it takes to push those professions up. Min/max later. Take the professions best suited for your character so you can gear them now. You'll still have gearing gaps, but at least they'll be smaller ones to fill. Sell the excess on the AH.
Play the AH. It's the only way you'll make money until you hit the Outlands where everything drops gold. If you don't need the drop, sell it on the AH. Price it accordingly. Do research on pricing. Sell your excess mats and profession gear. However you do it, the AH is almost mandatory.
On that note, take gathering professions for a little bit. Metal and leather are good, stable sources of AH income until you get a self-sustaining cash flow. I didn't have a guild or wealthy friends for my first character and I wasn't about to resort to begging, so I did this. I made an initial nest egg of gold using gathering, then switched to professions that allowed for self sufficiency in terms of gear. Now I've got play money and am decently geared most of the time. This is also why I have almost no patience for beggars.
But yeah, itemization sucks. Big time.