Ira and Roth IRA cap out at like 6500 for a year and the 401k tops at 22500. If he's retiring at 50 I'm assuming he's stuffing both.
Having said that, picking an employer based on vesting in 2 years seems inconsequential compared to overall compensation at one place vs another. Pick the higher paying gig, stuff whatever's leftover in a brokerage, and don't sweat vesting at all.