I've found soldier the best class to start out with. It gets you to work on predicting people's movements, managing ammo/ammo loaded, straightforward firing, and exploring everything in the process. Medics often make or break a team so it's not the most ideal first class IMO, since a lot of people get pissed at bad medics.
At least, I've found soldier to be the best first class for myself. It may be different with you.
As for the custom mapcycle so far, how about this for a preliminary cycle:
cp_devilsbrew1_3
ctf_2fort_night2_b2
pl_mill_b5
cp_follower_rc1
pl_swift_final
tc_meridian_b5
cp_pacman_wtf_normal
cp_roundhouse_1_2d
pl_waste_b4
ctf_waterhole_b4
cp_yukon_rc
cp_industrial_b6
pl_woodwind_b4