it's cheaper than buying your own checks, but WAY WAY more annoying. I don't recommend it unless you're desperate.
But if the bank prints you checks, you haven't saved any money.
Reading this post, I'm thinking I would imagine R would need large bills for tips, cash only cabs, and such ...
I'm always looking to break large bills. They are a pain because most of my cash needs involve small bills (tips, cash-only cabs, cleaning lady, street or green markets, etc). Why would I want to not break a large bill?
If I'm in a place that's likely to break a large bill, I'll often take advantage of the opportunity. The only time I prefer large bills is for holiday presents for my building's staff.