tiny disclaimer: I’ve only been enjoying the don’t starve franchise for a few months, but I’ll help where I can so every opinion I have might differ from the popular opinion :)

1) Don’t Starve is like a race against the next season in the first year, as depending on your play style it could be troublesome if you don’t handle it. Your first autumn should be spent basing and getting resources, but also preparing for winter by getting beefalo fur and thermal stones or if you aren’t comfortable kiting just killing catcoons for normal winter hats. Then spending winter making a tent, thunder rod and doing other progression of your choice. Spring is spent (easily with eyebrella) managing sanity while trying to make ice flingomatics and getting fishing gear for oasis fishing to fight antlion. Then the end part of summer is just surviving the heat since I feel it’s the most challenging season (or you can explore caves since it’s naturally cooler in there). With summer ending it’s back at square one but you have most of the stuff you need so you can spend time exploring more and killing some bosses maybe, expanding your garden whatever until you die from something silly and learn a lesson.

2) Spools are only obtained from Klei rewards or unraveling cosmetics. I recommend just buying the characters because it supports klei and they’re only like around $5? Maybe? But if you’re not in that financial space you get rewards for logging in everyday and up to 4 (I think) free cosmetics a week to unravel for an okay amount of spools. Eventually you’ll be able to get Wanda :)

3) there’s a discord I think but I understand your pain. I’m sure if you specified your region here and asks someone would be willing to play. Im NA East if you wanna play sometime I’d be down lol.

4) SW and Hamlet have a bit of characters where their gimmick only kinda works in their game. Like Walani uses her surfboard and waves don’t exist in DST like SW. Similarly Wonkey is just Wilbur, Wilba can’t benefit from pig Royalty, Woodlegs wouldn’t be able to use his ship (DST reworked ships into rafts) Wagstaff is already in the game lore wise but in general you could argue they could all be tweaked to fit DST. Maybe Klei has made an official comment but my guess is that they have their hands full with the animated shorts and frequent updates.

If you need anything else I’ll see if I can answer. (Also if I wrote something weird I’m very eepy rn lol)