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Oblivion's Thieves Guild actually makes you feel like a criminal

Been replaying Oblivion after a long Skyrim stint and I forgot how much the Thieves Guild questline just gets the vibe right. Like, in Skyrim you're basically running a criminal business - very efficient, very organized. In Oblivion you're actually sneaking around doing jobs for people who treat you like you're expendable, getting your hands dirty with blackmail and fencing stolen goods through actual fences who have restrictions on what they'll buy.

The radiant jobs feel like actual work too, not just "go steal this thing from this place." There's a sense of risk that Skyrim's jobs kind of lost. And the fact that you can't just waltz into the guild - you have to prove yourself through Armand Christophe's jobs first - makes joining feel earned instead of just... stumbling into Riften and Brynjolf recruiting you on sight.

Anyway I'm probably just being nostalgic but the pacing of the Oblivion guild questline hits different. Anyone else feel like the progression was tighter back then?
 
I get what you're saying about the initiation - that's legit. Having to do jobs for Armand before the guild even considers you does create this feeling of "I'm nobody yet" that Skyrim kinda skips. Brynjolf's recruitment is more about convenience than earning trust, yeah.

That said, I think Skyrim's guild questline gets unfairly dunked on sometimes. The actual story beats - Mercer Frey's betrayal, finding out the guild's been gutted, the whole thing with Karliah and the Skeleton Key - those hit harder than anything in Oblivion imo. Oblivion's jobs are fun but the overarching narrative is pretty thin. Skyrim made the guild feel like it actually mattered to the world again, which Oblivion kind of didn't.

The fence restrictions thing though, yeah, that's a real difference. Skyrim streamlined fencing to the point where it almost doesn't matter - you just sell stolen stuff to anyone with the right perk or fence. Oblivion made you actually plan your fences and work around their inventory limits. That's a systems thing Skyrim lost that I do miss.

Honestly the real problem with Skyrim's guild isn't the questline itself, it's that there's nothing to do after Trinity Restored. Oblivion at least kept feeding you jobs. Skyrim just... ends. You're guild master and then what, radiant jobs forever? That's where the "running a business" feeling breaks down for me.
 
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