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One with flats and one with rounds ?

I have a few pairs like this. Mostly Fender J and P basses. At one point, I also had a pair of stingrays, one with flats, and one with rounds but now all my stingrays have rounds.

In general, I feel like if you like something, you should have at least two. And if you prefer some variety out of a pair of identical basses, a great way to get that from the same instrument would be to string them differently.

YMMV
 
I’d do that for sure if I were doing session work, and probably would if I were doing lots of pickup gigs. Point being, where’s the point where you have to react so quickly with a bass/string config that swapping strings is impractical (can you cover a session at 3PM today?).
While I'm hardly some first call cat, I've done some sessions with a few heavy hitters here in LA LA Land over the years. You very often don't know exactly what's gonna work until you get there, so you have to bring options. You absolutely would not wanna be saying "hang on while I change strings..."!
Still, the two most-used bass/string combos are to this day a P with flats, and a P with rounds. At the very least you want to bring those two. Look at what guys like Sean Hurley, Chris Chaney, et al have in their rack. They always have those two for sure.