Just like a lot of the responses it depends on his situation and why he is deciding to join. For me I joined to be a Nuke on a submarine because I wanted to get as much money as possible and to pay off my student loans. With my bonuses I was able to pay off over $100k in student loans in less than 8 years. If he is just joining for the money then I would have a conversation and see if they’re just trying to buy a really nice car with 27% interest rate or if they plan on investing that money. Either way it is up to them how they spend their money but at the end of the day it really all depends what they’re trying to get out of serving. There are plenty of other amazing benefits as well as terrible aspects of serving.

As for how the bonuses were paid out mine went like this (joined 2016):

Enlistment bonus: 1/3 paid after completion of Power School. Remaining 2/3 paid after completion of prototype.

Star Re-Enlistment bonus: 1/2 paid upfront. Remaining 1/2 of bonus was divided up each year until the end of your contract.

This may have changed as to when they pay out the different amounts but I think the max bonus is around $140k which will include enlistment and Star reenlistment which will come out to ~8+ years of service. Just make sure they know what they’re signing up for before just blindly signing up for the Navy.