I'm by no means a wiring guru, but adding connectors into the signal path increases the chance of signal degradation. Impurities in the contacts causes loss of signal, etc. I would suggest that you get the length of cable for the longest run, and add 10% at least. You can always coil up excess cable (properly, mind you). If you have equipment in only one rack, you only need to run it to that rack, if you have two separate racks, you may find it easier to run two separate cables, one for each rack. Yes, the quality of the cable is a big factor. You may choose to have someone make the cables for you. It may cost more and you have to be very sure of your cable lengths but the cable will have been tested and you should be able to take it back if things aren't right.