How much can you ask for in a contract for reenlistment?

Not at all, you should aslo ask for a promotion and pay raise while you at it. And the bonus should be $20K, we don't have enough qualified soldiers attending RASP now days. And tell them that you will not sign a new contract unless the army meets your needs and demands. The Pentagon will not hesitate to meet your needs and give you what you have requested. If your retention NCO and career counselor refuse to write up the contract, go to the next one, untill it gets done. Good luck in your future endeavors.

Contracts are based on what the Service needs/wants at that particular time, and it can vary from month to month based on numerous factors. You can ask for the world, doesn't mean your are qualified, or that it is available. All you can do is ask.

You can ask for one option: duty station, stabilization, or training.
Bonus is based off a chart that lists MOSs by rank. If your MOS and rank gets a bonus you get more the longer you reenlist. The bonus and the option aren't tied together meaning that you can get a bonus as long as your MOS is listed, regardless of the option you pick.
Your career counselor is not a negotiator or someone you negotiate with. We work for you and will give you everything your authorized, but we can't do anything more than what policies authorize us to do. It's not like the MEPS where you can demand something and we make a phone call and it magically appears. If
Also, RASP is a Selection not training. If you want to go to the 75th Ranger Regiment, put your Man Pants on and email [login to see] and they will schedule you a RASP date. You never need to reenlist to attend any selection, only after you've been selected.