I am thinking about cutting all my cat5 cables that I bought from Monoprice to the exact length needed and to crimp on a connector. Besides the typical difficulty in crimping that connector, does anyone see a problem with this? Will the type of cable be okay? Will the connectors fit? And so on............
No issues with doing this at all. The key is have a RJ45 tester available so you can test each crimp of your RJ-45 cable. As far as difficulty in crimping, shouldn't be that difficult with a decent crimper. The hardest part is remembering your standard colors and making sure you are consistent with them on both ends of the cable (that is why I recommend the RJ45 tester).
As far as cable, Go no worse than cat5. Avoid solid core (go stranded) as it does not like to be handled and tends to break when used for something other than going into a wall or a data center.
Any connector will do and you can get them relatively cheaply at any electronic store or online store. Make sure they are RJ-45 jacks and check to see they are compression crimp types (there are others types of crimping out there that you do not want to mess with.)
There is a slight art to crimping these cables, for example, make sure you do not strip the plenum too long as it will not provide any strain relief to your 4 pair wire. The strain relief comes from the crimp where the crimp actually grabs the gray/black/white sheath around the wires so that when you plug it in, the strain is on the outside sheath and not the 4 pairs of wire. Another is to make sure you have straight cut across the 8 wires so that they lay flush against the top of the jack (you should be able to look at the jack--assuming it is opaque-- and see the shiny copper dots on the end of the individual cables. This means they are far enough inserted into the jack so that the vampire tap will get a good bind on the copper.) Again, double check you color order and make sure the wires did not twist while you were inserting them into the jack. They tend to do this and can make for a bad crimp.
Good luck!
Kurt