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[MrFlibble]

Daggerfall has quite a few weird little things like a faction member/affiliate that says s/he knows nothing about that faction (I think same things may happen if you ask for directions, although it is kind of strange to ask a shopkeeper, for example, for the directions to the same shop you're in, but anyway), most of which probably come from too much content being dependent on randomization. This is noticeable with both NPC dialogues (I've observed some NPCs randomly react oddly, for example telling the player not to talk down to them when addressed in the "Polite" mode) and quests. In general, I'd say I have the impression of the game being somewhat half-baked in that a) it is very obvious that many more features were planned but some got cut or were never completed along the way and b) the game shows different styles and design attitudes that come from different periods during its development. The latter, for example, manifests itself in the lack of consistency in graphics and art: on one hand, there are hand-drawn sprites for most static characters, while monsters and moving NPCs/opponents are pre-rendered 3D models; on top of that, different character images of both types vary in sizes, resulting in a visible difference in detail, especially in close-up view. There are also some minor but very annoying graphical errors and glitches here and there, in characters' clothing, armour and other things.

Random dungeons are another matter. At first, they can be very confusing altogether, but very soon it becomes obvious that they are made of pre-set segments that are more or less easy to familiarized with. This fact, however, has both positive and negative sides: once you see a familiar part (even if wall textures are different), it's pretty easy to navigate, however the pre-set segments themselves are pieced together in a random pattern, so you may never know where you find yourself next. After some time, dungeons become familiar enough to feel repetitive, yet random and unpredictable enough to get annoying (especially on closely timed quests).

This is not to say that Daggerfall isn't an enjoyable game. It is. But it could have probably been a lot better if the developers spent more time on polishing its mechanics. Overall, I find the review of the game by Theodor Lauppert pretty insightful:

I have made the experience that the games I love most are all what I call "if only" games. Sure, they are good, enjoyable, but they could be so much better if only…

Not only is Daggerfall no exception, it is actually the best example. Technically, it is not even a good game. This huge world not only lacks variance, it is illogical, inconsistent, and everywhere the game mechanics that should be hidden are plain to see.

An important aspect of gameplay are the randomly generated quests you can get from guilds, merchants, and nobles. They get repetitive quick, and the few that are actually interesting sub-stories are often buggy beyond playability. Dungeons quite obviously never served any purpose but being dungeons in a role-playing game. Travelling overland you only have the choice between walking/riding right through the countryside, which is beautiful but difficult because there are no roads and you will probably miss your destination, or "fast travel," which deprives you of any random encounters and completely takes away any feeling of distance. You can climb over city walls right in front of the guards, but resting in town is regarded as a serious crime. The houses you can buy are practically useless—all you can do in them is rest and drop stuff on the floor,—and the ship, though useful, does not behave even remotely like a ship and is, unless you set your own rules, mainly an official cheat.

But despite it all, the game can keep you playing for hours, days, months. Why? I guess it is simply this fascination of living in a virtual world. It is the basic concept that, even if not executed well, makes this game unique and well worth playing.

[Japo]

Originally Posted by MrFlibble

I've observed some NPCs randomly react oddly, for example telling the player not to talk down to them when addressed in the "Polite" mode

That's because you failed your Etiquette skill check. It could be a logical reaction from someone whom you're addressing in an inappropriately pedantic tone for example. By speaking in a polite or blunt tone you can get a more favorable reaction (depending on whom you talk to), if you pass the skill check; but if you don't you get a more unfavorable reaction than if you had used a normal tone. Overall, pretty useless.

[MrFlibble]

Originally Posted by Japo

That's because you failed your Etiquette skill check. It could be a logical reaction from someone whom you're addressing in an inappropriately pedantic tone for example. By speaking in a polite or blunt tone you can get a more favorable reaction (depending on whom you talk to), if you pass the skill check; but if you don't you get a more unfavorable reaction than if you had used a normal tone. Overall, pretty useless.

I've also thought about that being a game feature It's still a bit weird that someone should consider politeness as "talking down to them", but I guess those peasants and townsfolk just don't know manners

Speaking about weirdness, I remember a merchant quest where I had to deliver a false letter; in that particular case, a love-letter from a girl to her fiancee had to be replaced with hate mail. During the quest, I had the options to ask people around for the whereabouts of both the girl and her addressee, and I indeed found them out. However, I could not tell them about the false letter (I decided that completing the original quest and replacing the letter was such a bad thing to do), so finding them was pretty useless. The quest description at UESP Wiki also does not mention the possibility of revealing the intents of your employer to the people involved either.

[Japo]

I think I read this in the game manual--if it wasn't on the UESP wiki. Also both skills aren't equally appropriate: polite/etiquette improves nobles' reactions, and blunt/streetwise the commoners'. It's probably not impossible to get a benefit from talking in the wrong tone to a person, if you're lucky, but if you try to talk politely to a commoner you're liable to get just that result.

About the quest you can't be sure that it's a feature instead of a bug, what will how bugged the game is, in particular in that area.