@BigSlick4523 unless you've got a hot $.25 frac you can't live without, why not do $.50/$.50 like
@Nine_high and
@LeLe suggest? When you're tired of making change for your inebriated friends and there's two grand on the table, what's more annoying than having them bet in $.25 increments? Meanwhile, you don't need as many $.50 as $.25 to make the breakdown function well and that frees up valuable real estate for workhorse chips.
Plus $.50/$.50 really doesn't play any bigger than $.25/$.50 so your guys won't be as tilted as $1/$1 (which would do wonders for your 400 chip breakdown as well as your change making concern but come with raised stakes and less BBs).
If I had to stick with 400 chips (which seems unnecessary in your situation) perhaps I'd go with 60/120/180/40 of $.50/$1/$5/$25 for bank of $2,050. Still rather light on $1s but workable. On the rare occasion you need more bank, keep using $100 bills. First 10 $50 starting stacks of 6/12/7/0, then 10 x $5 for the next 11 buy ins, 2 x $25 for last 20 stacks.
With 500 chips, I like what
@Nine_high suggests with 60/170/200/60/10 (which is close to your own proposed breakdown but with 20 less fracs and 20 more $1s). Again, I'd sub in $.50 for the $.25 fracs.
But as you say:
So why take divert any chips away from your workhorse $1s and $5s to hundos that you rarely if ever need, especially since you can just bring in $100 bills?
With 500 chips, I'd focus more on the playability of the set for most situations instead of more bank for rare situations. Perhaps something like 60/170/230/40 (again substituting in the $.50 frac with $.50/$.50 blinds) for bank of $2,350 or 60/200/200/40 for a slightly smaller bank of $2,230 that has more $1s in circulation to make it a little easier to make change. If needed, you can always use $100 bills.