I'll defer the S/W piece to someone else.
As far as checking your connection...What I used to do in the field (in a pinch) is once you have crimped the headshell inspect the bottom of it (the side with the clip) and make sure you can see the copper teeth on all the pins poking thru the wires. Sometimes if you don't crimp hard enough they wont sink all the way through and possibly not make an adequate connection.
Once that is complete...plug it in. You won't get a link light on your DTE/DCE if the cable isn't built properly.
Now like I said, someone will most certainly recommend a piece of software to monitor your bits across the link for errors. but if you are connecting say router to router you can just check the physical interface attributes on both ends while spooling up some test traffic on the interfaces.
oh yea...Don't forget to use the proper wiring standard when building your cable... You can just Google it. Here is an example of T-568A & B