I wouldn't be stripping the outer sheath at the entry point, which sounds like your hinting at in the post?
Cable anchors for multiples, maybe finger trunking if you have a large cab and lots of wiring, agree with JW there is practical tidy and overboard.
Think about if when your finished it looks like it would be a PITA to add/remove/replace something while still keeping tidy.
Keep the data lines free and flowing make the powers short and together. You will know if you are happy with how it looks if your not do it again. Imo never make cables too short. Im not a dressed fan imo it has to be functional and practical. Stand back after and either be happy or move stuff and redo it