Yup, a very light mist of Super77 over the back of the stencil, give it a minute, and stick it onto the canvas. Put a piece of paper over it and apply pressure over the area to stick it well to the canvas. Don't use too much 77, start out with a light mist, and work up if you still getting overspray. You'll get the feel of how much you need it soon
Never tried the pyro cutters (i'd be interested in how they fare though), but yea, 5mil is a bit too thick for x-actos without massive strain like you said. My suggestion is to go to 3mil, and use a swivel-knife. The advantage of swivel-knife is that you are shearing the plastic instead of cleaving it like with your standard No.11 X-acto. (By shearing I mean this: you know when you can cut a sheet of thin plastic with open scissors? just kinda running them through? That's what I mean, you don't have to exert barely any force)
Yes, I always suggest low-pressure matte sprays. You have no idea how much easier your life will become. I'm partial to Beltons, because they have the finest pigments in the land, I've never EVER clogged a greydot cap with them. Mtn94's have slightly larger pigments, sometimes prone to "wisping", but they have certain advantages sometimes, namely, good coverage, absolutely dope pinks, and they can be dripped with mineral spirit. Beltons use some weird nitro-alkyd as the resin, and it can only be dripped with acetone or MEK. You can spray with Rustos (I do) but you have to spray from like 2 ft away. Finally, I recommend staying away from the new Krylons, the ones with the useless 360 nozzle and watered-down over-pressurized consistency -- use Rusto "Painter's Touch 2x" instead for those needs.

*Edit:
> what do you spray on to not make everything around sticky?

I use Nylon Gloves with PU Palm and Ghetto Spray Booth to contain the spray indoors.

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