Bookworm

I'm most interested in cutting vinyl for stickers for skaters. I've noticed a lot of the decals I have aren't as permanently sticky as regular stickers I get from other companies. Are there any vinyls with some seriously sticky backing?

I have some shirts that I'm 99% sure are vinyl graphics (since the guy who made them also does vinyl decals) and the graphics have been very durable through multiple washes and plenty of hard days of skating.

Looking around it seems like I could do some pretty neat stuff with a vinyl cutter. The ability to create low-volume runs of shirts is also appealing to someone trying to grow and market a business. This has been very educational. are there vinyls available with hi-tack or permanent adhesives? I've found the decals my friend cuts aren't the stickiest.

Vectorizing images is something I hear about all the time but don't really know anything about. I understand some image formats (.pdf, .ai) are "vectors" and others (.jpeg, .gif) are not. I use the GIMP image manipulator, can I create cuttable designs myself in this program? I was reading and saw that just because something is in a vector format doesn't necessarily mean it's cuttable, what are the things I need to watch out for? Thanks!

I've been googling and searching around and I can't quite seem to find what information I'm looking for (maybe it's right in front of me and I'm just dumb) I'm starting my own skateboard bearings company, and I'm a huge fan of die cut decals, the kind that come sandwiched between two sheets of plasticy stuff (more vinyl?) I have a buddy who does decals but boy does the price of these things add up fast (he charges $0.07 per square inch), and since I'm mostly giving these things away it kills me to see that these stickers cost ~$1.50 (sometimes more). I've also always got ideas for my own designs that would be fun to cut out. I can't seem to find what you need to do to cut the vinyl and place it in that "sandwich" that decals always come in. I'd want a cutter that can do 24-30" width so I can do some large car-window stickers as well.