To answer your first question, yes, it is straightforward. Use good materials and good assembly technique and you will build a cable that outperforms and outlasts what you buy over the counter. I've built them for a load of folks here and on the old DudePit and between me and people like Butch over at Bayou there are a lot of folks who have firsthand experience with hand assembled cables using Canare or Mogami cable and Neutrik, Switchcraft, or G&H... connectors.
The trick is to not damage the braid. This means removing the outer jacket without nicking the braid, and then serving the center conductor through the braid with minimal damage to either. Do that and you have the basis for a rock solid connection to the connector, both physical and electrical.
I use a utility knife to score the jacket (start by removing about an inch), then I use a pointy solder probe to open up the side of the braid just above where the jacket ends. Push the strands apart to make a smooth hole that is about th width of the center conductor insulation. Now kink the center conductor so the hump is exposed through the hole and use the pointy probe (spudger) to open the braid up a little more. Now you should be able to get the spudger under the center conductor and pull it through the hole in the braid. VIOLA! Be sure to strip the black covering from the center conductor insulation. Just the lightest pressure with the blade of a utility knife will score it without damaging the underlying insulation.
Use clamps to hold the connector and cable in position while you orient everything and solder. I also use a mini hemostat to hold the braid in position. That stabilizes the assembly and makes for rock solid contact between the braid and the sleeve connection. That is the same whether it is a monster Neutrik NP2RC or a Switchcraft. The idea is to have the wire making solid contact with the plug during assembly and not have anything moving around.
Enjoy. Chris at Redco has been a great help to me in getting the right parts and supplies, and they make great assemblies as well. Markertek out of NY has also been an excellent resource, but they have minimum shipping fees and can cost a little more depending on where you are and the size of the order.