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.

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.

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 would need to check with your retention NCO to see what your options are. If what you’re asking for is available based upon the needs of the Army then you’re straight, however the best way to find out the availability of what you’re asking for would require you to review your options with retention.

$5 Billion dollars!

If you don’t ask I’m supposing they’re not offering.

They have set scales - your negotiation is limited to YES I like that or NO I don't.

Bonuses are determines by hrc. Your mos might not even be eligible for one. Btw, the Army owes you nothing, even a re-enlistment is not guaranteed.

Usually you only get one of those. It also depends on why in out calls for that mos and if that mos is eligible for bonus.

You can ask for whatever you want.

What they have available changes frequently. I saw a lot of guys reclassing with their reenlistment, and their new MOS came with a bonus. I would go that route and then drop a RASP packet, maybe in AIT.