Always good to be contrary, if we all agreed on everything this whole forum would be pointless
I don't think 95 is impossible if he stays fit and has the right role. Stringer injury doesn't hurt his cause. Nor does Rutten seemingly wanting to go down the "let's get cute" path after so artfully avoiding it last year with the whole Merrett at HB thing.
Hardest part for Caldwell will definitely be that his kicking is going to make it hard for him, it's not impossible and Hopper/Taranto, two similar types, both averaged 97 last year.
I guess the hard part for the Caldwell pick is that ideally I think you want a higher ceiling than 95+, realistically you'd want him to look like a 110+ capable guy, which leaves you a lot of room for failure on your outcome before you've got a failure on the selection. If it's 95-100 that's your realistic aim point you're basically not leaving any scope for error before the pick starts to go bad.
I really like Caldwell though, hope he can stay fit and have a run at it and would be happy to be wrong, if for no other reason than I've got him in a couple of my keeper leagues, but I think he's a very high risk starting pick in classic. FWIW, if he was a forward I'd almost certainly be picking him so it's not that I think he's bad as much as the midfield requirements make the successful ending a lot harder to obtain.
Having said that, the winner last year had Taranto and I'd argue Caldwell has the same upside scenario as him, possibly better because he's not that bad a kick, and he's cheaper, so logically there's zero reason he can't be part of the winning side! As much as I think we can overrate how hard 95+ actually is, we also tend to overrate how bad the M8 is in most winning sides