GIMP Version: 2.8.14
Operating System: Windows
GIMP Experience: New User

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So I'm working on some 1" tokens for a tabletop game and have a few questions about how to get everything resized and organized for printing. If I change the print size of the images I'm using to 1"x1" then paste them together on a single canvas will that cause the individual images on the page print at the size I want regardless or the on screen size? or will I have to resize them as well? Also what size of canvas should I be using? I'll be using standard 8.5X11 US letter sized paper

I don't know for sure.
But when you set up new image, you can switch to 8.5x11 inches instead of pixels.
Then in Advanced options before you actually click OK to create new image, you can set dots per inch (DPI) settings.
Then what I would do is print a single test page and see if it's actually 1" like you want.
Then based on that test page, you can make appropriate settings.
Because if I went to Staples to print it out, there's options to print and then fit to page which might blow it up larger or shrink smaller depending on how large the image is.
Always test because there's so many different things that can change by the time it turns into physical printing.
Also I tried setting 300 dpi once, and it was too fine for Staples's printers, so I had to go home and change to 150 dpi.