When layering all of these pieces do all of the hoodies bother you? Seems like the bulk behind your head would be irritating.
Anytime I have layers with multiple hoods - I put the hood up (over my head), add whatever layers & put up hood for each piece I have on, then as last step: take the single formed hood off my head. Not sure if that makes sense, it kind of layers the hoods a little. [1] this allows me to not have any bulk between my shoulders under layers (hate that) and [2] I now can layer for my head as needed as well - meaning what's my protection objective: sun, concealment, wind, warmth, etc
I used to hate hoodies - but I'm becoming a believer. Still try not to have too many of them on at once. I have the new Apex hoodie to throw into the mix for this year, so we'll see how it performs. I imagine I'll still switch to mid 1/4 zip as my base layer for any later (cold) seasons. Unlike the heavyweight series, I can still put on some miles with it as a base layer in late seasons.
I keep trying to like the Fanatic, mainly because I want the pocket, but twice now I've sold a Fanatic hoodie.. I can't stand the wrist on em. It has that built in glove/thumb hole design. Silly if you ask me. It's just over-engineered in my book and as result uncomfortable to wear when gloves aren't deployed. I'd rather just wear the core heavyweight hoodie & either put my hands in pockets or throw on some gloves. Some people swear by this article of clothing however.
As for "must haves"... Pants - tough subject, everyone's different. With the Ascent (latest model) and Timberline I can do anything Colorado can throw at me so long as I have a bottom base layer in my pack. Don't waste your time with Sitka's core bottoms & take a look at Kuiu merino 210 or similar. Why Sitka is resisting a full-zip model is beyond me. I'd kill for core heavyweight with true full side zip - adding & removing base layer without taking off boots is a game changer in my book. As for "star performer" items, I agree the Kelvin Active is worth twice it's weight in gold during fall archery season.
It's easy to buy items you don't need, I'd start slow and get familiar with the products so you can identify a good deal in used markets (FB buy/sell/trade groups & eBay).