I have always been a huge fan of D&D style derivatives, but I have never actually played D&D itself. (Baldurs Gate (I & II), Final Fantasy VII+, Magic the Gathering, Oblivion, Fallout 3+).
My friends have convinced me to play my first campaign with them (I don't know much more than that), I told them I wanted run-of-the-mill D&D (3.5), no cheesy gimics when possible. (I want it to be hard)
I know this is a very open question, with a few parts, so try not to blow up at me after the first sentence(I am only 1/5 through the 3.5 core "manual"):
What are some general character genres that might be typically reserved for mid-high level veterans?
I want a D&D character that is going to give me a hard time, but can achieve functional synergy if played correctly. I don't want the strongest class, or the most brokenly powerful . I am looking for something that requires careful balance and tactical execution. Doesn't need to be fun (the harder I have to work, the more fun I have).
After overviewing the manuals, my attention is first drawn to Bards and Rogues. But I start getting lost in the specialization/multiclassing decisions. And while I'm sure I could mash together a crippled Thief/Bard on my own, I don't want to be an jerk to the other guys.
- I like sneaking - I like traps/poisons/buffing/debuffing - I like micro-managing my strategy and execution at all times
My favorite playthough in Fallout New Vegas was: sneak, unarmed, and explosives (with lockpicking and science as minors). I ran around naked with a backpack full of mines and a handful of grenades. (even then it was still easier than I had hoped, even with a difficulty modpack!).
My last playthrough of Skyrim was: sneak, alteration/conjuration, and alchemy (with minors in destruction and daggers). Ran slim on armor (so I could swing my dagger while quickly running backwards), using glyphs and summoned creatures to stage my ambushes. Boss battles would require crazy amounts Master Health Regen and Master Magic Regen.
Neither of the previous descriptions were particularly powerful, and in the hands of most casual gamers would have led to many rage-quits (only because a winning synergy took more patience and discipline than they were willing to put forth).