I've decided I've been hijacking enough threads and I'll start my own to assemble all the info I'm curious about.

First some history- Two bikes ago I had a 12 FLTRX, through it was great and had the dealer build me a pretty angry 103 because I wanted more power. .010 over 11:1 pistons, MVA heads, 260 cam, 58 TB...all the parts you'd want to throw on a 103. Well, I thought so. It made good power but it was a chore to ride. Hated that. And it used a pretty good amount of oil - more than I'd like. Not that you'd be surprised by that.
My last bike was a 14 FLHXS with the stock 103 HO, Power Duals, HO slip ons and a stage 1 flash as the only performance mods. honestly this was a lot nicer to ride than the build 103 and I was *kinda* happy with it. For all intents and purposes, I'll admit the exhaust was "too big" and there was no actual tune done to the bike. So that's my most recent baseline.
My Riding style: I can count on one hand the number of times I spin the bike past 5k every year, I prefer to roll on the throttle to pass rather than downshift, I ride 35% two up, we're a combined 340-ish lbs. I also treat my bike as an appliance: I want to start it an go, not mess around with things, expect it to run perfectly every time and change the fluids at recommended intervals. I was NOT cool with adding a quart every 1500 miles.
Fast forward to Christmas: Bought myself a brandy new 2016 White CVO Street Glide and now I have to decide what it is I want to do for the next three months it waits for the weather to clear.
I've already purchased the Jackpot 2:1:2 header and V&H 450 Titan slip ons. I do realize these are "big" and I should probably be looking into 2" baffles for my stock mufflers. I'm thinking about it, but I'm also thinking that I really like these 450s. Lets press on.
So I"m down there talking to the guys in the shop about possible power additions to the 110 while it's sitting there looking pretty all winter.
He suggests bolting in the 585 cams. I look into it and find that yes, they are an upgrade however they like compression. Especially when you're talking performance under 3k...where I spend a lot of time.
So I go back and have them put a package together with pistons (22503-07B) going for 10.5:1 .010 over - says he'll order them .010 over and final cut/hone the stock jugs to make sure they're fit like they should be. OK fair enough.
Then I start reading more and asking myself questions - if they're going to cut the jugs anyways, can't they cut them .060 over and pop in 4.060 pistons - thus making a 113? In my head, I assume the extra displacement will further help the low end performance of this combination.
In my mind, I have three options:
1) Tune it in stock form and enjoy it - it'll still be the best performing bike you've owned.
2) Go 10.5:1 on stock 110 displacement with the 585 cams.
3) If possible cut to 4.060 and go 113 - assuming it would run even better.
I'm just not sure about a bunch of things:
A) Is it possible to just cut stock 4" jugs to 4.060 and pop in new pistons (22571-07B) and have a 113? Is it really that easy?
B) Are there reliability issue with the idea above vice staying at 110 ci? Not sure how thick the spigot is in the stock jugs.
C) Since I spend most of my time rolling on around 2500 and shifting at 4-4500, am I looking in the right places for touring torque?
D) Will I be happy leaving it stock with a tune? (I know you can't quantify this - Read: Will it really be a significant improvement over my "stage 1" 103 HO?)
E) If I decided to stay with the 450s (and I do plan on it) - do you think swapping the slip on's out to a set of 2 or 2.25" baffled stockers would drastically affect the tune?
"While we're in there" we do plan on putting in steel gaskets, new lifters and the upgraded head studs.
Thanks for any input - just trying to bring my research and thoughts together on this deal.
-Matt