All right, apparently this is in the Game Room now, which had me really surprised for a while (I’ve had what I considered to be a much less nasty Cafe Society OP end up in the Pit), and then I saw how many responses there were, which had me totally surprised, and then I saw the responses…and…it’s a mixed bag. And very civil all throughout.
This is a really nice website. 
Anyway, I meant what I said, I’m not going to continue grumbling, it’s not good for you or me. I do feel compelled to address this one point:
I’m not here to denigrate anyone’s choices of electronic entertainment. If you find getting lost, losing ships, staving off mutiny by an eyelash, running out of food, getting stuck like a pincushion in sword fights, getting creamed in naval battles, getting creamed in land battles, getting rebuffed by snobbish governors’ daughters, getting the door slammed in your face by crown-grovelling Spanish merchants, not being able to find the place on the map, having the wind change direction to directly in your face, and retiring as a lowly farm hand for the 500th time fun, more power to you. Your life, your pleasures. I gotta ask, though: If this game really is so wonderful, where are the videos? Any game that players love, that becomes iconic, that’s captivating, visionary, groundbreaking, breathtaking, expansive, controversial, denounced, they will record it. Just think about all the Super Mario Bros. or Grand Theft Auto games you’ve seen in your lifetime, Tecmo Super Bowl, Baba Is You, Street Fighter 2, Dark Souls, Minecraft. The only things I could ever dig up from Pirates! (all NES version) were an incomplete career, a “quick game” challenge (farm hand, natch), and a bizarre TAS that was almost certainly made as a joke. Even The Oregon Trail has a few serious runs. In all, it really seems like that whatever challenge this game may provide, reaching a luxurious retirement…the ultimate goal…doesn’t seem to be worth it for a lot of players.
Airk - Looking back on it, I honestly thing the biggest problem was that from 1987 or so, I was an arcade guy, and (for the most part) the business model for arcade games was “go as far as you want as long as you keep shovelling in tokens”. There was simply no financial incentive to have huge stumbling blocks or painful requirements or near-impossible tasks. That worked for me, and even for the really expensive games (I’m looking at you, Crime Fighters), it didn’t feel like a complete screwjob, so the frustration never really built. I don’t remember a single time I’ve screamed at an arcade game (except for that one really bad night at the Beatmania IIDX machine, of which the less said the better), which was, regrettably, a fairly common occurrence for computer and NES games. Thankfully, it’s the modern age, where finding something that works for oneself is not a hassle, so I’ve decided to just put the past behind.
Male, BTW. 
hogarth - (I was going to PM you on this, but your account isn’t allowing it.) I’m curious as to which two Assassin’s Creed games you’re talking about. There are a couple that I’d consider relatively easy, at least regarding the main game, but I’m drawing a blank on an “insanely hard” one, or at least one that I can positively say is insanely hard.