I'm my experience, long term reliability of crimped stranded cable (that particular combo, to be clear) has lower longevity with vibratory environments.
There are some crimps that are great for stranded, but the RJ series (and others which stamp down) generally don't seem to be good enough.
Again, anecdotal, but yeah.
Ideally yes, but I've had to do this regularly for many services developed both in-house and out of house.
Solve problems, and maybe share your work if you like, I think we all appreciate it.