I don't think TSS day and dating was the problem I think you do. The problem is the first movie. For some reason over time it has been seen more and more as a terri-bad flop. Much of the time it happens that the second movie in a series takes on the momentum from the first. That's why IM 2 did better than IM 1 even though it wasn't as good and again, imo, why TSS did as poorly as it did. The day and dating hurt the Box Office, not the public perception of the film. I think too many folks had their minds made up before they ever saw it.
In this case it's unfair imo. TSS was for me a surprisingly enjoyable movie. Just as the Whedon/Snyder JL was a surprising waste of time. Anyway as always, YMMV.