Hip-hip-horay! (Of course, my official help has all left at the end of the school year and I'm stuck in lab from 7am to 7pm for the next two or three *months*. I'll have zero time to play now.)

I think you should play multiple characters to get a feel, but maybe play one character extensively to get an idea what the game feels like at higher levels? Not sure how fast you can level.

I'm voting for Charr Engineer and Human Guardian combo. As for what caster, I imagine ele is more up your ally than either necro or mesmer. So...yeah. I know, I'm not helpful. And you should make a dedicated GW2 tumblr for picture uploads. XD