This may be the outside scoop, so I beg your pardon if so.
There's a newer style of crimp RJ-45 / 8P8C connector housing which is easier to use. Unlike the ones that have been around forever, you feed the wires all the way through the housing, so they stick out the front a little. Then the crimping tool cuts them off flush while crimping the contacts.
I haven't used them - I share your frustrations with making cables, particularly with stranded cable - but they are apparently much easier to get a reliable connection with.
Might be worth a try. They're commonly labelled "passthrough" connectors. I'm not recommending this particular seller or listing, it just has some good images:


