How hard can it be to employ somebody who knows as much about re-enlistment, advancement, pro pays, and all the other pay schedules presented over a four, six, eight or more year career as can combobulated to help these young adults make choices they can be as content with as the needs of the Navy can allow?!?!?!?
Guys like myself and 'court can ramble on forever with the wisdom of years, but there should be somebody with contemporary and consructive data in front of them whom these first termers can turn to, something better than hyperlinks to pay tables....
We can't be their best hope, or so I would hope,.... 
As stated above, shipboard financial training is available on a voluntary basis. It also comes up during GMT every year (for an hour or two). NNPTC and NPTU both have financial training as part of student indoc. The CCC's I have known have all been honest, helpful and to a degree provide an objective opinion on the decision to reenlist. I've even seen CCC's recommend to kids to wait a year to re-up.
I know this probably sounds like I am just trying to parrot the party line, but I think the decision to reenlist goes beyond being a financial decision. I honestly believe the bonus should just be, well, a bonus that comes along with reenlistment, not the driving force behind the decision. The choice to reenlist should be more about either keeping a job you want to keep doing for another couple years, or about getting a set of orders you want. To STAR on the ship for the "money and respect" (yeah, someone said that) can lead to disaster. The last kid I saw STAR on the boat just quit less than two weeks ago, with just over one year on board. In June last year he was going to be the MCPON and in July this year he was going to the Chaplain.
When a SPU reenlists, he does it into a comfortable environment. He may not yet know the in's and out's of the proto-pal system, but he is familiar with the site and knows many of the people around him. He also won't go three section duty there or go to sea. Then he shows up to a boat with some experience at his job (and, sadly, the ego that goes with it) and just as much (or less) sea time remaining on the contract as if he had never re-enlisted.
When a guy reenlists at the end of his first sea tour, he is "senior" in his field and ready for a change of pace. He can also pull a sea/shore rotation waiver and wind up doing less time on the boat; often leaving the boat before he would have checked out on terminal leave.
When a guy reenlists at his two year point on his first boat, the time extended on his contract WILL be spent on that boat (at least until his 60 months is up) unless he can get a sea time waiver for P-type. When he extends for six years at the beginning of a five year sea time obligation that will also leave him without enough time remaining on his contract to complete a shore tour without extending or reenlisting again, or he will get sent to some crap general shore billet for refusing to extend for a full shore tour.
While this response goes too long, I think the financial arguement for reenlistment is probably the least important consideration to make. It causes people to jump into a job they don't like or can't handle just for some money, potentially causing them to wind up out of the Navy with a truck payment AND a bonus to pay back.
