I reroll a lot and start new alts, etc. I feel your pain, but experience has taught me that:

1. Items don't matter the first half of the levels - you can stick to using what you get from quests and drops. Upgrades won't improve your damage output and efficiency that much at lower level but leveling will. The xp you could have gained while asking for money, going to the mailbox to get it, shopping the auction house, then traveling back to the questing zone will be greater than the gains you get from using a slightly better level 20 weapon or armor.

2. Doing all the quests and selling loot will pay for training until you get gathering skills.

3. Gathering enough to keep up with zones and selling it on the AH via a mailbox/bank/AH alt will net you more than enough money for training and a mount when you need it.