I’ve been fanatic on the details for my retro wall insulation of my home. And I just realised I’ve dropped the ball with the roof. I read a article or two that made my anxiety go through flying higher than said roof. I need help right away as the renovation has just started. My zone 6a 1953 home is getting the walls filled with Fiberglass, taped zip, taped 2″eps, tyvek drainwrap with rain/bug screen topped by lp smartside.
The unhappy gable roof has a poorly vented attic and asphalt shingles. Site built truss, and YIKES damaged top plates all sliced up (You can check previous post on that fiasco) I’m closing current vents in favor of ridge with soffit, stripping everything off including my abused T & G  sheathing. Replacing with 3′ ice&water I think, zip, fanfold, and I’m embarrassed to say I wasnt paying much attention to my general contractor about the roof… I think he said something about felt but I’m not sure! I’ll call him right away at 9am! All topped off with Pro Snap brand hidden fastner metal roofing from Menards home improvement store. 
I just read about condensation issues with metal roofs and I immediately panicked. My attic has issues that are already improving but maybe not enough! 
First off, insulating the roof is not an option at this time. Bearing that in mind:

Question 1) is my roof under planned and headed for trouble with the current plan?
Q 2) if so, what is the cheapest plan I should follow instead?

Attic issues past and current:
I bought the house in august. Previous owners “fixed leaking roof” during their 10 years ownership.
Issues I’ve been working on since august:
-The asphalt shingle roof is a trophy winner for worst build.
-Unvented wood soffit covered by metal perforated soffit.
-The space in the eaves/exterior top plate was purposely blocked with wadded up insulation paper (maybe they thought it would keep the house warmer?)
-Every rafter has been sistered to create length for a retro fitted overhang, these people cut or notched the top plate in every rafter bay to make room for the additional sistered on wood.
-the site built truss have been worked on by someone to strengthen. They built a addition and tacked a new roof onto the older roof. 
-I’m finding a few cracked supports that will be replaced during reroofing.
-unsealed diy install furnace hvac & ducts up there built to touch the roof deck in spots. Today is actually the day it gets unplugged and removed. Ducts & new 98% just installed in the basement!! (Neighbors also informed me previous owners used to keep the outdoor ac unit up there as well!!!)
-Gable venting with diy box vents thrown anywhere high or low without reason and leaking water.
-bath fan venting inside attic
-loose fill mineral wool smashed flat under kraft faced batt insulation that faced whatever way it landed when tossed in.
– mold. Here, there, little patches everywhere. 
-Frosty nails dripping away.
-and 100% unairsealed ceiling.
-damaged cloth wiring everywhere! (Yeah, wiring update will be finished in two days)

Yeah, and my home inspector said it was in great condition!
Anyway it is close to being totally fixed of all of those issues except I cant do much with only 2″ of space for insulation & 1″ for vent baffle at the eaves. And the partitan wall top plates do not reach the attic, they are covered with ceiling sheetrock. I guess they raised the ceiling 1st before walls back in 1953? So I’m sealing the ceiling seams instead? Huh, idk. 
So… yeah, issued. But almost all fixed. I’ll triple check all airsealing spots as insurance.  
Soo…  I was busy with the attic and forgot about the roof, if you feel me? Do I need to change plans? Talk to me goose! 🤔