Since you're sticking with the monk here is my advice:
1) Every time you log on, look for a group. Once you get one, don't autopilot through. Setup the appropriate macros, be engaging, and do everything you can to be the best monk possible. This will build up the reputation you'll want and help in the long run.
2) Friends everyone you group with that is worth a damn. Keep in touch and invite them to join you often. Grow your network of contacts and with that, plus your solid reputation as an amazing monk, you'll find tip #1 easier to achieve.
3) Try not to be too overly gear-focused. Loot what's fair, roll on everything that is greed, and spend on a budget while you level. When you are 50+, then you can monk PL twinks to bankroll that high-end gear you'll need later down the road.
And I can't stress #3 enough. You'll make money gradually over time, and there's a ton of cheap items that you can afford as you grind your way up. You can even take up tailoring and make yourself a set of Wu's, snag a cheap weapon or two in EC (lots of choices around 50-100p), and that'll be good enough for some time. If you get hung up on solo farming one mob just because it drops a sword that sells for 5pp each time then you'll really hurt your leveling speed (once it goes light blue / green) and it'll make #1 and #2 difficult (you'll be grouping less and the contacts you did make will probably out-level you).
Or at least, that's how I'd do it (and did on live). Not to mention, you can't factor in unexpected donations. On Fippy (the progression server on live) I had a 60 monk run across me in Field of Bones and just unload his gear onto me and quit. You can't plan for stuff like this, but it happens!
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