The being a small feet guy is something that could end up being solved. At www.dravesarchery.com and www.travelcountry.com they have some M38 and M39 in various styles <ASK through the messenger thing they have>. They are on sale, i think.
I'm reading, that for some, the socks influence sizing of their vibrams, for others they don't. But if you wear socks of different thickness, doesn't that matter regarding the fitting of your VFFs?
If the socks are thick <ex. wool> and your foot is on the big side of the size, they might make the shoe feel tight, but it depends on how the shoes feel/fit before the socks ans how thick the socks are. I do not use thick socks with shoes, only medium to thin ones, the thicks socks are reserved for very cold nights in sandals .
What? speeds with insoles? All the speeds I have seen have the insoles stitched as part of the shoes. I wouls like to get some speeds with insoles like these.
The pressure: is it towards the leg? is it towards the floor?
the initial feel could be of pressure but being towards the floor because of "bulkie" toes. As I first tried them on I felt that I had to go up one size, but when I went up one size they were too big; that is on the treks. On the other hand, when I tried the same size on komodos, perfect fit, meaning that each model has some different fit. If the pressure is towards the leg -> lengthwise<-, then you could be needing some upsizing. In that case, no matter how you stand, sit or walk, they are going to be unconfortable. How long are the toes after each size is about 1/4 inch, give or take, so you could have to trie some bigger to "feel" them and check if it is a size thing or a feel thing.
About the toes, that happens to many of us, my pinkies are 1/3 empty, so not to worry, your fit is fine if the big toe and heel are where they have to be.
About the first question, imagine as if you were the big bad wolf when he wanted to catch little red riding hood and walked forefooted to get near her without being listened.