DEL has it right on all this... 1) if your cable sheath is too soft, use the rip cord instead of a score because the score will often hit the conductors; 2) pulling a cable is where the damage is likely to occur - it should really be tested after the fact. 3) strip what you need to so you have working room - then untwist your pairs, get them straight, then trim them down to the 1/2" or so with the D Snips - then slide into the jack or RJ45 and terminate. Keep the untwisted section as short as possible - IIRC, spec is < 1" total untwisted (both ends combined).
This is an area where practice makes perfect. You don't have to do 1000 ends to get the technique down - you should be able to get a basic feel for it pretty quickly, always improving. This reminds me - when I was young and stupid, I used to make my own patch cables too for the office - I literally sat around my coffee table in the evenings while watching TV hand making 250 3' patch cables because I was redoing the network at the office. Beyond stupid - but it sure locked in my technique! Sometime during that I bought my current crimper and some of the strippers (that same Harris brand I've used forever; lost some to airport security, other techs, etc). I've since taken on pros who do this for a living - particularly when I'd get someone b*tching about my chosen Siemon jacks being harder to terminate - and shown them how it's done. Of course now if I need patch cables, 100% of the time I'll order from monoprice. I don't even reuse cables - with any sort of cleanup project, I throw out what's in use and buy new now. Almost any time I waste my energy on the existing patch cords, I end up regretting it.
I do a ton of work now with Ubiquiti ToughCable Pro - Cat5e with the same + plastic inside from Cat6 separating the conductors, plus a cross braided layer like you'd see in Coax, plus an aluminum (I think) foil wrap... this has protection in that it's UV resistant, can handle hanging down a tower; rodents can't really hurt it; and the protection and shielding eliminates static buildup outdoors - all things kinda necessary for long outdoor runs. Talk about an art form - take everything you know about regular terminations - then add these in - you have to still get things to fit inside the RJ45 (shielded - or wrapped in metal) - and get the drain wire terminated in the special spot on the RJ45 - ensure that the foil is in contact with the metal on the RJ45, and often add a boot.... I have quite the special routine dialed in now for it...
I'm still no help with test equipment - I won't go on a job site anymore without my qualifier - and mine is on the lower end - a
Fluke CableIQ - (I also have another that'll test POE and can do VLANs and ping a router, etc) - if you do any sort of work by the hour, then you need that - mine has paid for itself hundreds of times over now in saved troubleshooting time. Absent that, I'd check into DEL's recommended tools or at the very minimum, the monoprice tester that's ~$75.
All this stuff adds up, but to me it's an investment. For instance, when I was doing remodel work on my house - I could've bought the $100 8" Ryobi mitre saw - but instead I chose to spend more like $1100 on the 12" compound sliding mitre saw and the proper stand for it - overkill for a lot of what I do, but having the correct tools means that a job takes a fraction of the time AND comes out significantly better. If I buy a tool, it's my intention that it'll be the only tool of that style I buy in my life - the one that works perfect and will last a lifetime.
/ramble
Reminds me of when I was a kid learning to play the guitar before I got sufficient finger callouses. I guess there's no tool for that, eh?
