Nice, sounds interesting!
Pokemon aren't that hard to draw! Just try!
The key thing to remember is that instead of trying to make it perfect, make it really sketchy. Hands look best when you spend less time on them. :)

1 and 2. The flying machine was actually going to tie my character's history as he would have a horrible accident which would partially explain his un-likable attitude and metal arm and eye-patch. Yeah, i wanna make him kinda scary.

3. I was going to have probably 2 or 3. I will be unable to draw them. Since I have enough trouble drawing humans.

4. I'll dry. I draw sketchs in my leisure. Rarely skilled. I can't draw hands X__X

1. Yep. Think Leonardo da Vinci but less wood. I have a very crude flying machine style if you click here but there's also the flying bicycles, airships. Ever seen Treasure Planet? I wouldn't mind a steampunk surfer as well. If your going to have a flying machine, make sure you have some kind of explanation why. Unless you have an amazing reason or you already designed it and it looks awesome, couriers are the only ones I am accepting to have flying machines. UNLESS YOU WANT TO BE A BREEDER which we seem to have a shortage of SUs.
2. Yes, you can. The only thing I'm not allowing to happen to the human body is genetic modification like giving powers or Pokémorphs. You could have an iron lung! Just remember that having a bionic arm would make your character heavier and if you wanted a flying machine, you'd have to take that into consideration.
3. Yeah, I don't want to limit people too much on this RP. Creativity is the key and I want to make sure people can design stuff and be as creative as possible. Since you can't actually keep Pokémon handy in a Pokéball, I'd recommend 2-4.
4. No! I would LOVE to see you draw something. Like I said, be as creative as possible! I hope MORE people draw characters, Pokémon and scenes, no matter how crap they think they are. :D

I got a character idea for you steampunk RP, but I wanted to ask a few questions before I set anything in stone.

1) Steampunk culture has flying machines right? I remember see a few in some of the stuff I've seen but I wanted to clarify it.

2) Do humans receive similar cybernetic enhancements to Pokemon? Like metal arms and stuff?

3) How many Pokemon are we allowed to have? I didn't see a number but I could be going blind for all I know.

4) Will you laugh at my poor artwork if I do attempt to draw my character? X___X

Umm I think that's it. If I have anymore after those, I'll run them by.