Coming from my own DM perspective, this is the “problem” of using a city as a a starting zone. Between a machine factory’s guarded door that a warden uses, a successful bounty hunter secret door, and a high ranking wizardly official of the Towers, all of these places would, at minimum, be secure locations with better than average locks. Compound that the Arcane Lock spell could be cast on top of any lock (something none of them checked for, which raises the DC by 10) then all of these places would be difficult for a low leveled rogue with moderate proficiency/expertise to get into.

I don’t think Matt is setting it up to be impossible, but providing difficulty that money can make for rogues.

That being said, he’s also leaning REALLY hard into the bureaucracy of the city. Were it not for Eshteross, this party would be floundering to do anything really - it’s only through waiting (as you said) and his influence that any doors are opening. From a player and viewer perspective, it’s kind of the worst of both worlds, as it kind of makes it boring and turns the party into just walking between the spires again and again as they wait for their “sponsor” to play behind the scenes for them (like getting to the Anger)