Consider this thread stuck (the S&S section doesn't have a comprehensive sticky yet, but once it does (if I ever feel bothered enough to do one, or if anyone else wants to volunteer...) I'll move this thread out of the sticky category and link it (to save some clutter).
Comments:
Sheers: I think these are incredibly convenient. Even a cheap pair of gardening shears from a dollar store will do just fine. The nicer ones are probably just a little more comfortable, and the blades stay sharper longer. I also noticed that the cheaper blades tend to "warp" from the strings snapping.
Guide awl: I have never NEEDED this tool. I think if you think ahead a little bit, and know how to use your simple tools (pliers, a little force, scrap string, etc) you should be OK without this one. I can't even recommend a pathfinder awl as a convenience tool in most situations. I think YL got it right tools you "MIGHT" want to consider.
Parallels: I use these all the time, and they are GREAT! However, the parallels you linked aren't so great. I have a pair, and the action on them is WAY too stiff. The serration is very aggressive. i've snapped quite a few poly strings on the tie off(s), but I always give a little slack, so it's never been a problem. If you can find a gently textured pair of parallels with a spring action, I bet you'll be happy as a clam with them. A substitute for these is a starting clamp, although I think a nice pair of parallels (or even better: CAM assisted pliers) is a nice luxury to have. (It makes the job more convenient and enjoyable! invest!)
Flare it: It works alright, a heat gun is helpful, but I don't like the potential crushing of a frame. The twist down force is much higher than people would think! I have one, but rarely, rarely use it.
Awl: I'd like to point out (haha, get it?) that the length suggestion also goes another way: If the awl is too long, it is likely the taper is too mild, and it won't be useful for wiggling around in a hole in the case that you need to enlarge it (not so often, but it does come up). As far as bending motions, you're right, it shouldn't be used with much force, but there are cases where lateral tension is applied (i.e. when installing a bumper strip). Too thin of an awl in that case is really frustrating. I like the TW awl, but haven't had the pleasure of trying the GSS awls.
Starting clamp: I can't say that this is a necessity in terms of: if you don't have one, you can't successfully string a racquet, but I can't imagine stringing without a starter. I (now) start my crosses using a starter. i've had several, too: the Gamma clamp (3 spring, SUCKS), Alpha old clamp (RAB/Alpha non branded, 2 spring), and the new alpha clamp. Both Alphas are excellent, and I don't really have a preference, but I definitely think the newer alpha is more aggressive. A balance between the two would be nicer.
Callibrator: it's the tool that you should consider buying even though you will rarely use it. 'Nuff said.
Tools you need:
Cutters: yes, the xurons are nice, but there are other options out there that do the job JUST AS WELL (quality wise, really!) as the xurons for tennis related purposes. Just google around for flush cutters, there are several options for cheaper. (Not that the xurons are out of the question in terms of price). I found a nice set of tools at home depot, although they're not available on their website any longer. i bought them two winters ago, they were the crescent flush cutter/mini plier set. The flush cutters have a similar styling to the xurons, if not slightly more flat, for a better close quarter cutting surface. the mini pliers are extremely thin, and slightly textured (not really serrated). They grip string VERY well, and give plenty of push-power. They're also extremely nice to handle. And since i don't use my pliers to tighten my knots, they work perfectly in my stringing 'system'. I personally HATE the cutters and pliers (sears brand) that you mentioned, but to each his/her own! (Also, I don't think serration is a bad thing, i think it translates to less physical force required to grip a string securely, I find this important in maneuvering a string through a blocked hole at times).
OK, commentary aside, enjoy the sticky status!