Well…I had a whole other door-to-Madness open up on me this afternoon that I never saw coming…
The pairing of shoes and board is something that is often overlooked, but I think it does deserve a bit of consideration.
I used to always wear skate shoes in size 11 to skate in, then a mix of 11 and 12 for work (all still skate shoes, mostly Vans but some others too over the years) until I developed ingrown toenails, especially my right / back foot big toe nail, so then would wear 11.5 when I could get them but gave up and have pretty much just gone for 12 now.
At first they were way too big, some more than others, but then my board also started to feel small when I was in anything other than 11s, so I ended up going up a board size too - now around 8.5, or DLX 8.38, but also branched out to have 8.75 and others on the go too. Maybe my foot shape has molded more to the bigger shoes, because they don't feel half as big as they used to, or maybe I am just more used to them, but flips are almost non existent in bigger shoes.
Some shoes will work way better on some width boards, some shoes just don't seem to work as well, so as I still have a lot of 11 and some 11.5 shoes, I skated in those today, in thin socks and everything on any board just felt so easy, balanced and the shoes felt thin enough to get a lot closer to the board.
Those same boards had felt almost awkward yesterday in some 12s of a different style, but both were still the regular Vans vulc soles, so there shouldn't have been much in it.
Long story short, yes different shoes will make a board feel way better, or not so good, maybe more so for some people, or even for what you want to skate, eg having a flat ground session in thicker shoes might be easier, having a transition session in thinner shoes might also be easier, but thin shoes when I am trying to do too much at a skatepark or street type stuff is just a bad combination usually.
I also wonder if the current state of the shoes makes much difference, eg newer shoes work better for more rolling around and not doing a whole lot of tech stuff, just nicely broken in shoes are best for the tech stuff, maybe a little more worn in for transition, but also sometimes well worn shoes with new grip on transition is good, but old shoes on street just hurts, unless I am only rolling round a carpark trying to break in new bushings or something similar.
* For you Sk8 Hi on bigger boards, Old Skools on smaller boards, might be the winning combination there, until the thinner shoes start causing too much pain to your old injury... Who knows though!?!