Reached the point of nearly 3 full resets of the new season and raid tier, so time for an update...
Esmënet (Hunter)

Cleared normal LoN in the Exiles social raid 3 times. Also killed the first boss on HC 2 times and Carnage 1 time.
Have 15 completed m+ pug keys, and 2 disbands. Taken it slow and incremental key level increases as normal for me.
Have done 13 tier 8 delves.
Done a smattering of overworld events/quests for gold and some herbing and mining.
4-set, 658 crafted weapon and a fair amount of good champion pieces otherwise. Except trinkets and a neck, which is why the overall iLevel isn't very high. Have something like 6 copies of the worst possible delve trinket on champion track, and one of them on heroic track. Bit of a repeat of the first tWW delve season where I just got the same pieces over and over and over. Which made me stop doing delves, and I doubt I will keep up with 4+ delves a week next update on this character...
Esmë (Paladin)

Done 20ish tier 11 delves, Gallywix on story mode, 2 m+ dungeons as Retribution in Epiphany guild m+ night group and 8 m+ dungeons as Protection in scheduled m+ groups with RaeSea.
Has 2-set, a 675 crafted weapon and 658 crafted shield as the main highlights gearwise. Neck and cloak currently veteran track, rest champion or hero track. So the most stacked character I have at the moment.
It's been fun playing with only friends and in a limited capacity again. I also enjoy the Templar hero talents more than the Lightsmith stuff which was very clunky.
Wutteät (Demon Hunter)

Done 9 tier 11 Delves, Gallywix on Story mode and a single pug m+.
Crafted a 675 and a 658 Warglaive from Delve crests and put two hero track items in the catalyst for 2/2 set. Not had much luck with gear from the content nor vault, but also small sample size.
Vengeance seems pretty fun as usual, and playing without addons on the character makes games sounds less annoying so much more zen when playing.
Esmëralda (Mage)

Pugged the first 3 bosses in LoN Normal, done 2 m+ pug keys and 8 tier 8 Delves.
Has 4-set and a crafted 658 staff and has a general good spread of champion pieces. Just haven't farmed the crests to spike the overall iLevel.
Frost seems more fun in dungeons this time around, not sure why. Might be because Frostfire is in the vogue.
Not really having an aim with the character, but want to have reasonable gear at the end of the season, and keep in the Mage loop. Simply because it's fun to play.
Esmënehr (warlock)

Done a bunch of undermine world quests, some overworld events and the weekly dungeon quest for rep, gold and tailoring/enchanting materials. Decent raw generation with not much time/effort needed.
Done all the LFR wings once and the timewalking event last week. Got 2 tier pieces in the vault, but little in the ways of getting gear outside of it. Also did Gallywix in Story Mode for the Enchanted Crest.
Mostly played Destruction with random talents as I haven't done anything that requires output. Watching Chaos Bolts and the low APM required is nice for the stuff the character is doing.
Content opinions with changed time frames
During the start of the season, I went from having a lot of spare time to having very little outside weekends. So besides the "I want to do what is fun" some amount of "is this content useful for character growth" entered the field. So here's what I prioritizing with limited time:
3 tier 11 bountiful delves (1 with bounty) on Esmë the Tank and 1 whatever delve I use the item that summons the Underpin (normally also an 11 bountiful). [Best value crest time in game, despite delves being boring for me]
A scheduled m+ session on Esmë during the weekend, ideally 4 dungeons. [Weekly highlight]
A round of herbing/mining of about an hour with an audiobook on. [For the chill part and prevents draining the coffers of gold]
An LFR wing, all the world quests/dailies and the weekly dungeon rep quest on Esmënehr the Warlock. [Gold generation]
Some tier 11 bountiful delves on Wutteät, pug m+ on Esmënet and maybe pug some normal raid on something if I have leftover time. For reaching some pve goals in the long run.
Currently I need the better part of a weekend to get all this, so I might have to go back even on this reduced scheduling...