Nice presentation..
I'm a consultant.. it's what we do! 
A couple of points (just my thoughts) Rather than an 8:1 mainsheet I'd go with 6:1,
Yes... absolutely right... started drawing it out and realized that 8:1 is overkill...
but with a short fine tune as well.. that could be 4:1 and give you lots of power for the last few inches of trim. 8:1 is going to mean an awful lot of
line to pull through all the time, and it will be slow when the loads are light.
What would that look like? How do I rig in a fine tune? I think I've seen something like it before but I can't get my head around it right now..hmm
You appear to be planning stoppers/clutches for the pole down/lift... I think they are a bit too awkward to use readily and often, fairleads and camcleats can be arranged to be easily released and re cleated even from several feet away in the cockpit. I'm not at all sure that you'll need a
winch... if you double your downhaul at the foredeck you should be fine on a 34 footer - just don't let it get away on you.
Great... thanks for that... I think I'll go with that approach...
You may find the mainsheet hanging in the companionway a bit of a pain and often out of reach.. but you've not got a lot of room left to run it forward and back like it probably is now.
I think that's what I'm going to end up doing... I have mixed feelings about a mainsheet not being "handy"... (probably from my 420 days...)
It's rare but I've seen mainsheets run aft along the boom with a
cleat on the boom more or less overhead in the cockpit. Problem then is access when the boom is outboard going downwind - you'd need a pretty long tail.
That would be strange... I have a bimini top and the clearence is already limited so that's not going to fit but thanks...
Anyhow, good luck and hope it all works out for you.. that's a fair bit of hardware you're planning to buy!
Yeah... thought I'd make sure I had an "Ideal State" designed before I just started fixing one thing at a time...!