Hope your step-son is over the worst now.
If you want to stamp on the bag or stamp on other fabrics to stitch on it my go-to ink is Versacraft - iron it once it's dry and it's permanent and will do fine when you need to wash the bag. I've used it on a pocket stitched to a bag made from the leg of an old pair of jeans and it worked great (pic attached so you can see - Midnight Blue and Cherry Pink inks if I remember rightly).
If the bag is a reasonably coarse canvas texture, you might do best to stamp on finer-weave fabric and stitch the bits on rather than stamping on the bag itself since the texture will affect the quality of the impression you can get.
Other ideas would be ribbon or fabric flowers, images or text printed from the computer onto T-shirt transfer paper (check the instructions in the package for stuff like printing in mirror image and washing), zipper flowers and embellishments made from stamped shrink plastic (punch holes before shrinking so you can stitch them on).
HTH kick start some ideas - have fun with the project!
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