Dean:
Check out Waytek for all your wiring needs. They make a whole bunch of vinyl wiring sheaths that work great. You have to buy some large sized rolls of it sometimes, but it is worth every penny.
I bought like 10 different sizes and every one of my wires or bundles of wires goes thru them.
You try and get as close as possible to the size, then coat the wires in dielectric grease to get them to slide thru.
Then use the adhesive lined shrink wrap to seal things up. I used insulated crimp on connectors that I also soldered for good measure.
If you want to get really crazy (don't ask me how I know) you can use marine grade wire by Ancor Marine that is tinned for it's entire legnth, or can be purchaed allready sheathed with different types of wires and colors inside in different gauges (West Marine carries it). They also carry a great line of marine fuse boxes by Blue Sea Systems that are great.
And you can seal everything even further by hunting down and trying different 3M electical sealants: paint on, rubber patches etc.
It also helps to use the Brother P-Touch 1/4" label makers, of the "flag" type, to label all the wires individually and in their bundles at the beginning, then one quarter of the way down, the middle, three-quarters of the way down, and then at the end. That helps a LOT when trying to troubleshoot, especially at the track.
Walt