Maybe for the sake of anyone who looks this up in the archives I'll post what I did for my final solution. Remember this is an RV7A and might not apply to other models..
1. Firstly I came through the rear bulkhead in the same location as Carl Morgan (the Kiwi)...extreme lower left corner (see photo). REASON: The Kiwis are pretty smart....and it means I can remove the vertical stabiliser without touching the wiring. It also means I can use a bushing through the bulkhead...I like that.
2. Secondly I routed the wiring up through an Adel clamp attached to the left bolt at the lower rudder hinge bracket. This positions the wiring to enter the forward end of the rudder tip. I also sleeved the wiring in this area. REASON: Wiring is properly clamped...no chaffing possible.
3. Thirdly I removed some of the upper lip of the rudder tip (forward end). I had to do this anyway because I found that the original tip was hitting the aft fuselage at full rudder deflection. REASON: Allows the wiring to enter the rudder tip over the top of the rudder tip without chaffing on the tip lip (no holes or grommets etc required in forward end of tip). Also enables me to remove the rudder by simply pulling the plugs out the back of the rudder tip.
4. Fourthly I used nutplates and ss screws and ss tinnerman washers to fix the rudder tip to the rudder. REASON: Good to be able to get in there to inspect the wiring...or to remove the tip for repairs if damaged.
5. Fifthly I installed an Adel clamp in the bottom of the rudder tip to direct the wiring as it enters the tip. It's an oversize clamp so it allows the wiring to slide but keeps it orientated in the right direction to eliminate chaffing as it enters the tip. REASON: No chaffing.
6. Finally I put a wiring loop inside the tip behind the Adel clamp. REASON: Allows me to pull out the light fitting from the rear to change bulbs without unscrewing the entire tip.
Here's a few pix to illustrate what I mean. You can left click on the pix to enlarge them and improve resolution.
Archive: tail light aft wire wiring route routing rudder navlight light strobe bulkhead tip fairing