SM gear? Luxury! When I hit Outland I had a grey belt with just 19 armor (no stats) and a mace that was a quest reward from Westfall...
Once you hit Outland, though, the first few sets of quest rewards will replace pretty much every item you had previously.

Luckily, with a multiboxing group, gear isn't a big issue while levelling - even with crappy gear my 5 shamans could blow things away before they got close.

As for cash - I had to "borrow" about 600g from my main just to be able to afford everything (including non-epic mounts) up to 60. It's tough on the bank account, that's for sure!