Does it raise a red flag when you deposit stacks of hundreds?  Would it help if we mixed in 50s, 20s, 10s, and maybe even occasional rolls of coins?  I am wondering if this makes large deposits less conspicuous or if it really matters.

Honestly I've mostly used $100 & they've never seemed to have a problem with it

Where do you guys get $100s?  All ATMs I go to dispense 20s only, even for large withdrawals. I'd be interested to know if providers hate to receive, for example, 50 $20s.

the drive-thru and ask to have larger bills.  Most banks are more than willing to exchange bills for you.

It shouldn't have "Monopoly" printed on it?

cash one of your own checks written out to you (or CASH) at the drive thru window. I put a post it note on it requesting 100's and 50s, depending on what's needed.