It's actually far easier than you think it will be! I recently started my first Alliance character (on the same server, but with no gold or heirlooms sent over), and I found myself making more than enough gold to keep up a profession and buy riding at level. The dungeon finder helps a lot with this, as it gives you good and sellable gear, as well as a fair amount of gold.

If you want to play it safe, pick up a gathering proffession and sell your cloth, and you will be fine.

As for me, I found the experience of starting over to be quite enjoyable, especially without the rush of heirlooms, it made me think back to when I first started the game. It's not like my new character is going to be my new main or even make it to 80, but whenever I need a break it's nice to have it.

I've done this a few times. It's easy if you've played for a while because you know all the best places to quest, how to work the AH etc etc.

However I just don't have a very large attention span and tend to get bored with the-

Oh look, a bunny!

I've done it a couple times...what usually happens is I go back and forth for a while playing my old toons and new ones. This time I've xfered one of my 80's with all the BoA gear I'd bought and a bunch of gold as incentive to keep playing on that server.

I started a new character on a fresh RP server for myself and found myself having no trouble. Actually just by RPing, my first encounter with another character netted me 25 gold from a very kind blood elf who was trying to earn the respect of my brother & sister taurens. My advice as a new character starting out is just pick up the gathering professions and even selling things like "Small eggs" can earn you some nice money.

Personally, I find it liberating! The challenge is refreshing and as a bonus you get to choose your new friends/guild based entirely on what YOU LIKE, without being held back or roped in by RL or in-game friends that are probably the reason you want to reroll ;)

I started a couple of characters on a new server about halfway through the expansion. RL was preventing regular raiding, but I could jump on and level for an hour or so when I had time. I didn't want to level on the same server (otherwise I'd be acutely reminded about all the awesome raiding I couldn't commit to), so I headed off to Arygos for a brief bit.

Here was my protocol (which worked really well):

1) Create the character you want. Don't log in.
2) Roll a death knight. Not as "the character I want", but as a seed character. Do the entry quests as quickly as possible.
3) Learn mining. Run around Elwynn/Durotar mining for a few hours. Sell copper on the AH.
4) Take the money from those auctions and buy four netherweave bags. Use the rest to play the AH or keep as an emergency reserve fund (you'll need it while leveling).
5) Send the bags to your new toon, enjoy leveling.

It's also nice to have a level 58-60 DK because of the holiday dailies. I think I got a gold per quest for doing 30 seconds of juggling during Fire Festival. Not a huge amount if you're an 80, but if you only have a level 17, any gold is huge...

I did end up going back to my original main, not because he was already semi-geared (honestly, I was in Naxx gear during ToC, so gearing up either him or my new 80 would've taken exactly the same amount of time), but because I missed the people in my guild. Not that the people of Arygos are mean or anything, it's just hard to find as a great group of people as my guild.

When I started a new toon on a different server, My professions were mining and jewelcrafting. I earned about 100 gold before level 20. Its not much, but way more than you need to start. Low level rings and necklaces always sell quick....imo

When I start on a new server, I create a DK toon and send it out to farm the easy pets. The raptors and the black tabby sell well for a start up fund.