It's excellent that games like this are being preserved, irrelevant of the legality. Old games need saving for future generations, and the Internet Archive are going down the right path. The emulation technology is still in early stages and some of the games are still missing sound or have bugged sound (like all of the Sega Genesis games) but hopefully given enough time they'll get them all working fine.
Assassin's Creed really needs to win the Take A Break Award from GB this year. I'd love to run around Victorian London but I'd prefer to do it two years from now and give Assassin's Creed some breathing room.
Ubisoft have long tried to strongarm players into doing what they want them to do; remember the Online Services Platform which forced you to play singleplayer games online? When AC 2 launched you had to be connected constantly. At least they were dissuaded from doing that, but Uplay is a less than preferable alternative.
Why do Ubisoft keep doing it? People keep buying their games! It's as simple as that. If Ubisoft feels they can get away with it, they'll do it, no hesitation.
Ubisoft's PC support has been very bad for a long while (remember, their Chief Executive said 95% of PC players were pirates). I'm not surprised they might be following in EA's footsteps and forcing people onto their little bit of software and off Steam. Nonetheless, it is irritating for the consumer who wants to have all their games in one place. Steam's authority must be challenged of course, but only through games sales, and Green Man Gaming and Humble Bundle do this very well. Uplay and Origin will always be surplus to requirements.
The letterboxing is purely and entirely a technical choice, I don't buy any aesthetic arguments (because personally, I think letterboxing makes stuff look like it was made in 1965). If it were aesthetic, it wouldn't be possible to do what you can do in the PC version: To run the game at a higher FPS and remove the letterboxing. Understandably Bethesda don't recommend doing this because the performance tanks (because they couldn't be bothered to make a 60 FPS fullscreen PC port). The Order: 1886 is going to do the exact same thing, for the exact same reasons.
Arguments for low framerates and letterboxing usually talk about making the game more cinematic or film-like, crucially missing one massively important point: It's a bloody game. We're not watching a film, we're playing a game, we want to swing the camera around to see everything. If it were a film I wouldn't need to twist my vision to see what was happening.