World of Warcraft alone would be worth a top list of most frustrating, yet most rewarding boss encounters. I just remembered Blackwing Lair back in the WoW Classic days, when it took us more than 100 tries each for the first two bosses (Razorgore and Vaelastrasz). 40 raid/guild members staying up all night, rezzing over and over again.
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Oh, no kidding! My "toughest" classic list has gotta be AQ40, getting attuned for Kara (ugh black morass!!), actually running Kara, and getting killed so many times by the elevator in Coilfang reservoir (technically BC and not vanilla but close enough). Thanks for reading!
WoW required players to have some nasty skills those days. Now everything is just mechanic, you can do anything you want with just one or two addons and lacking the proper skills.
It's definitely easier and more accessible these days, but I think a lot of the changes have been for the better. Learning talents from a trainer, leveling up weaponskills, and other things like that were just a lot of grinding. Blizz is a lot better about offering new and exciting content (even between expacs) to keep people interested and having fun. I remember in BC when we spent months bitching about the wait for Wrath, it took a while before they finally added the Isle of QuelDanas to shut us up. They seem to have a better handle on the amount of time to wait before adding new content, these days.
I personally like it better until BC, after that the game grew in it's story, but some things just stopped to appeal to me and after wrath I just lost close to all interest (besides as I am from Venezuela it became nearly impossible to continue paying the monthly fee)
If you ever decide to come back, look into the WoW token system. Basically it's a token you can buy with gold that is worth 30 days of gametime. The price is set by Blizzard, and it fluctuates but averages around 100k on my server at least. My husband plays enough that he's pretty easily able to pay for tokens for both his account and mine just with the gold he makes selling trade mats and other stuff on the AH. I don't think we've actually paid real money for our subscriptions in several months.
Talking about skill and AQ40, an old (2006) example of my former guild doing C'thun tries (sorry for the bad video quality):
I have a really soft spot in my heart for AQ40. The Paladin tier set from there is the first one I owned because our guild had it on farm after a few months, and it's just such a cool-looking zone. I still solo farm it occasionally, and can remember when I still had problems soloing the Twin Emperors. The fight with C'thun and the fight with Yogg-Saron (no lights) in Ulduar are some of my absolute favorites of all time. I think Ulduar was the last raid Blizzard designed that really captured my imagination. The raids in MoP and WoD were okay, but nothing really excited me about them. Some parts of Siege of Orgrimmar were okay, like the part with the water cyclone boss. Fighting Huolon? in the other MoP raid was fun too, the one that drops the floor out from under you.
I'm still leveling in Legion so I haven't tried any raids there yet. Got my demon hunter to 110 a couple of days ago, and now i'm working on my pally main.
I haven't returned to WoW yet. Maybe I will with the next expansion. Actually, I also liked playing Icecrown Citadel in WotLK. Especially, I liked to battle of the two flying ships, where destroying the other one was the task.
ICC is pretty great too, but I think I just got burned out on it after awhile because at one point I was running it on 3 characters a week solo trying to get the Invincible mount to drop. It is a good raid, though!