Sorry to hear it is giving you difficulties, Callidus.
Here are some tips- not being insulting- just that I actually own the original game...
Use the "M" command when in the city to get an overhead view.
Stores are orange, inns green, guilds blue. Houses (and the palace for some reason) are gray. The layout of Daggerfall city is NOT random, so you may be able to find a map online to use as a reference (ALT-TAB is your friend).
Here- in factWhile walking around, switch your mode to "Information (F3 in the default keyboard map). When you "activate" a building, it will give you the name and (if a guild or store) the hours it is open. If a locale is not open, you can "Loiter" for up to 3 hours at a time with no penalty.
Asking directions can be frustrating- "Just keep going southwest". However, someone will eventually say-"Let me mark it on your map."
That said, the only locations in Daggerfall city you HAVE to know are the Guilds, the Palace, and possibly a store or two. You may get "go exterminate the critters" quests directing you to specific houses or inns, at which point you do the "ask directions from lots of people" thing.
You SHOULD also locate The Odd Blades (most likely to have high-level weapons, even early in the game), a pawn shop (buys those high-value, strange items), and the Bank of Daggerfall (several locations).
Once a character has identified a building (either from information mode OR entering it), the label will always be on that character's map. Then you can take advantage of either running or riding your horse to get around the city faster.
Once you get a quest, it will show up in your log, including the name of the place and/or person involved.
Open up the world map (W key by default) and type in the quest location, then click on "Find". It will ask if you want to fast-travel there and offer options on how to do so.
A note on travel methods- you can chose "camp out" to save gold, but should always use "cautiously" when going to cities to ensure arrival when the gates are open. That matters mostly in Daggerfall, where Lysandus' ghost is a problem after dark. If you get "trapped" on the streets at night, just go to the nearest inn and either rent a room (if you are seriously roleplaying) or loiter the night away 3 hours at a time. Another option is to set your Teleport locus inside a guild and zap to it...
I have had one crash with this version running in DOSBox, which is MUCH fewer than the common Crash-to-Desktop issue that happened in the original game.
If you have questions, please ask- I will do my best to come up with a good (and possibly even CORRECT) answer.

ETA- Now playing "Trey the Reset." Because I picked the WRONG Temple to join! He has been lugging around a wagon-load of ingredients, waiting to get access to the Potion-maker- except Kynareth is one of the TWO Temples that does not HAVE one! So- Trey the Reset is now a worshipper of Stendarr. Which is cool, because you get a percentage chance per level of not being killed (except by drowning) whenever your character dies.