Just use your judgment. After looking again at your pics, in one, it looks like there's no reason to go past the body line. There's a good amount of paint south of the line that you can blend into. In the others, you're really close, so it's better to go past it. However, in either case, I still wouldn't tape right on the line. Either stop short of it (an inch or so) or go past (a couple inches.)
Just make sure you use good painting technique and you should be fine. And if you screw it up? It's not that big of a deal. Wait for it to dry, strip it off, and try again. As for the paint shop not getting the color right, well, I guess test the heck out of the paint before laying it down on the car. As I stated, because that section of the car gets little sun, it should be close to the original factory color, which unless the formula of the new paint causes a change in color, it shouldn't be too hard to match based on the original formula. My local shop mixed up several rattle cans of Frosted Teal Poly for me and it matches really well.
I should ask, did you use cheap rattle can primer or did you get something decent (SEM or something equivalent)? While I haven't experienced it personally, I've read and have been told that Krylon (or something equivalent) is not good to use under good automotive paint. However, if you may end up painting the car down the road anyway, perhaps it won't really matter....