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So I've got two ideas of what I should be doing:
There's a crease forming just below the toe cap, is there anything I can do to stop it?
Yep, talking about calf. Specifically a pair of dark brown Red Wing Beckmans and a pair of black Wolverine 1000 Miles.
It would depend on the model, but I'm pretty sure neither of those are calf. I think most 1000 Miles are Horween Chromexcel, but they make shell versions and maybe some other types as well. I'm not sure what the Beckmans are exactly but I doubt they are calf. I have a pair of Red Wing 9105s and all I've ever done is just condition them. I actually just use mine as a true work/woodworking boot so I'm not too concerned about appearances as long as the leather is healthy.
I'd just use conditioner and a creme polish as needed. There's no need for a wax polish since you're not gonna be able (or even want to) raise a shine on those. They are boots, I think they look better with some wear. If you are wanting info on a sealant wax such as Obenauf's LP or Sno Seal, maybe someone else will chime in as I don't really have experience with those. You definitely don't need to be using a wax polish though.
Probably not, if the leather is dry try nourishing it...otherwise stop calling it a crease and start calling it character and it will seem better..
How is the fit of the shoe?
Bick 4, maybe?