I've done some poking around today and I read somewhere that being a thief can actually be something of a job in Daggerfall because of the sheer number of homes. This piqued my interest: I have yet to play Skyrim, but thieving in Oblivion left me pretty unsatisfied because of the repetitive randomly generated content, and thieving in Morrowind just never really grabbed me. So I'm tempted to try out Daggerfall, but I figured I'd come here to ask a couple preliminary questions so that I don't take the time to install the game, DOSBox, and all that only to find myself disappointed later on.

1. I've read that much of Daggerfall is randomly generated. Does this mean that rolling a thief (and when I say "thief" I really mean it; I mean a character who spends most of the time sneaking around and stealing [censored] as opposed to sneaking around and killing [censored]) will be as unsatisfying in the long run as it was (at least for me) in Oblivion?

2. I've also read that rolling a straight thief makes Daggerfall one of the hardest games you'll ever play. Is this true? Should I attempt it anyway?

There is a pure theif, and then there is a person who has larceny in their nature. That latter will do OK, the former will not, out in the wilderness. In the towns, doing what you propose, you should be OK.

It is hard to describe the incredible size and scope of the towns of Daggerfall. You have to see it to believe it. However, most of that content is randomly generated, I don't remember the random interiors having much to offer. But, there are many named buildings that have more stuff in them. I did not break into a lot of houses in that game, so I can't really say if there is anything of note to steal in the generic houses.

Playing as a pure thief in Daggerfall is a good way to die a thousand times. You will end up developing either some tough combat skills to survive or becoming awesome with magic. There's no way around it if you want to finish the game. The dungeons are just nasty.

Stealing from homes is generally a worthless endeavour because you'll never find anything to steal unless the thieves guild sends y ou on a quest. Those are like the guild jobs in Skyrim, but too easy becasue cities are unguarded at night and NPCs don't move around inside buildings.

Stealing from stores is an option, but is essentially impossible to do without getting caught. Of course, you can just break into a store at night (with magic because lockpicking is frustrating at best) and take everything with no consequence. Then you can sell it back to the same guy. Yes, this is more of an exploit.

Really, I don't find being a thief in Daggerfall to be very interesting. It was fun in Morrowind because the shops and homes had unique items and hand-placed clutter. It was awful in Oblivion because nothing was worth stealing except on a guild quest.

The problem with thieving in dagger fall is that stealing from shops is nearly impossible without getting caught, and breaking in at night is basically cheating(0% chance of being caught). And shops are nearly the only places that have anything to steal.

Plus, sneak seems to barely function in the game so backstabbing is difficult to do reliably(not to mention that I can't imagine dungeon crawling in this game while sneaking).

Ditto CCNA's comments. Aside from the occasional random treasure pile, there isn't anything worth stealing in houses unless it's placed there as part of a quest. If you're thinking about playing the game as a Thief-class character, it is the hardest way to play the game. It can be done, but if you've never played Daggerfall before, you're raising the frustration factor exponentially.

Hitting up a poor person's house isn't going to net you anything, you've got to rob the rich places. I'd say a thief character is not the path for a first time player since a certain knowledge of the world is very helpful, but my favorite character I've played in DF was an Argonian thief who wore leather armor the whole time.

I don't even know how these other posters think playing a thief is all that tough, you can start with an ebony dagger and stack your sneak and backstab skills pretty high right from the start. I backstabbed skeleton warriors in the first dungeon, and the infamous imps. Do be warned though that lockpicking is an intelligence skill for some reason in Daggerfall and Morrowind, meaning you can't use intel as a dump attribute that you drain as low as it can go to boost your important attributes if you want to pick locks. Which is ridiculous. Somehow both of those games thought that lockpicking should be associated with your mana pool? Foolishness.

Stealth works fine, and backstabbing is especially easy with bows. Illusion magic can get you Shadow and Invisibility spells to buff your sneakiness. Lockpicking does svck.

But as for crime options, shop-catburglary is the only way to go.

Somehow both of those games thought that lockpicking should be associated with your mana pool?
Perhaps they were thinking that lockpicking required knowledge of how locks work, thus Intelligence. I don't know much about lockpicking IRL, but I do know that locks can behave very differently from one another, and you have to know what kind of lock you're working with to even begin to pick it properly. I mena, yeah INT controls your magicka pool, but it's also just a measure of your smarts.

Going full on thief was always my favorite in DF. The options for thievery are not all that exciting (pick pockets, B&E, wait in the shop and steal them blind), but something about accumulating piles of gold and treasure in this game by breaking into the various stores just felt so rewarding. Backstab and dodge are your friends.