Should I get a keyed chuck for cordless drill?
I have a hand-tighten chuck on my cordless (a Makita) and I've never had any issues. However most of my bits are spin-resistant (i.e. they have chamfers). I've used it with a step bit to drill 7/8" holes through stainless steel.

If that drill has a user-replaceable chuck, you could always just start with the stock one and upgrade if needed...