Broken record: foot pain keeps me from skating more than anything.
Shoes that err to the larger size are essential for me.
I completely agree with several pairs of shoes in rotation. I think that practice also challenges the feet in a positive way, but what do I know.
What cupsoles are winners? I really enjoy LRAB, but like to switch it up
@OK when you say you have several pairs of shoes in rotation, do you mean that they are dedicated, "skate only" shoes? If so, I totally agree. If not, if one is in the financial position to justify doing so, I've found it's good to have shoes only used for skating to avoid the midsoles being crushed out.
With respect to cupsoles, I've had great experiences with Joslin's (both 1's and 2's, though I prefer the 2's (which have sadly been discontinued)), the soles last forever, the uppers are durable, and the support/cushioning is great. They run TTS.
But the trade-off, as you may know, is that you will lose a lot of the board feel you have with vulcs like LRAB.
I just copped a pair of Tiagos but haven't skated them yet (still breaking them in). Will let you know how they turn out. They seem super cozy at the moment and very supportive.
EDIT:
I hesitated to list these, because they seem to be quite polarizing on the forums...
...But, WRT to wide shoes, I've also found that AREth cupsoles are great. I've worn them all day for work (on my feet), then skated them (yes, contradicting what I previously said, but that particular day I didn't have my skate shoes with me) and my feet felt great.
The uppers are treated with DWR so they don't stain as easily, they come with two sets of laces, an upper matching patch of leather (unfortunately no vegan options) if repairs are needed, and the soles are also durable - at least the gum soles. The model I have, the Bulit, reminds me of an IPath Cat (except with a one-piece toe) or a Lakai MJ Stay Flared (except with a cupsole)
YMMV, but from my experience they run between 1/4 and 1/2 size larger than most major brands, and I think are only made up to size 11.