I can't answer your question Zane, and need not try now, anyway as other more experienced people have now chimed in. I'm glad to have raised the issue, because it really is unsatisfactory, but more than happy to bow out regarding the solution.
I would say, if you want to follow David T's advice just start by changing to a smaller diameter sheet or get a bigger diameter clutch. That's where 90% of the problem lies I think. You really don't want to reduce the diameter of the sheet - not because of strength but more for comfort on your hands. I agree it is much nicer to have the sheet coming back towards you alongside the hatch. Its just that those big clutches are terribly expensive, the extra blocks at the mast do add a little to the friction, and it gives no mechanical advantage. Agreed, it is tidier and nicer - and I can imagine and believe it would be better for ocean sailing to be able to do everything from the hatch.
Plenty of boats manage their sheets at the aft end of the cockpit and as you are not ocean cruising, you will be mainly sailing from the cockpit so what I suggested is cheaper and simpler and you can try it for yourself without irreversibly changing anything. I'd still do that first, just to see how you feel about it, nothing to lose. Dave W's variation of it might be better I don't know, but that might mean re-arranging your sheeting system and that's OK but then you need someone like Paul or David W to help you do that.
Everything on your boat is to a high standard and with the best of gear, so I suppose you will want to keep up the standard, go with David T's sheeting advice based on proven experience. I don't have deep pockets so in that case I think I would replace the clutch with a simple decent-sized cleat, at least for now. If you belay minimally, its just about as quick and easy to release. But that's just me.