I rate the Thieves Guild DLC very Highly but I have a few Suggestions for Improvement and Growth

dodgehopper_ESO

I wanted to start off with a positive statement about the Thieves Guild DLC and simply state that I quite enjoy it as someone who enjoys stealth gameplay, and I believe it finally added something meaningful and entertaining above and beyond the foundation that Legerdemain first gave us. I'll just post my points right away from here.

1. I believe going forward the story would be more compelling (and fun) if we could start to gain control and unite the various outlaw dens under the control of the Guild. From a gameplay perspective this would make it possible to do repeatables from different locations, rather than travelling from Hew's bane to Grahtwood to Hew's bane to eastmarch to hews bane to elden root and so forth. I have a hard time understanding why the Thieves Guild should expect us to constantly be using jump gates to reasonably accomplish goals (I know we're superheroes but still).
2. I would like to see a heroic alternative to the Thieves Guild. One of my biggest problems in the storytelling of Skyrim was that unlike the Dawnguard Expansion, much of the game leaned toward the spectrums of mercenary to villainous to diabolical. Pure heroes really seemed such a rarity, and storyline options for such were greatly diminished. One simply left the story hanging without any meaningful alternative in the Thieves Guild of Skyrim nd likewise the Penitus Oculatus had a very weak storyline when compared to the Dark Brotherhood. The Iron Wheel of Taneth might very well have been a fantastic storyline alternative to playing the role of Thief. I'm still hopeful something along these lines is possible.
3. More Heists. These Heists remind me of the Thief series (Thief: Deadly Shadows) and so forth. I would love some missions that instead of setting a time constraint gave us difficult objectives that used interesting tools (like in the thief series). They are fun as they exist now, but I could see great room for improvement and expansion here and the Thief game, Styx, Shadow of mordor all offer great alternatives and choices, which could very easily be given via Active Skills in the Thief Line. I would like to see primary, secondary and tertiary objectives (again players of the Thief series will know what I'm talking about, and honestly after playing this DLC I assume the devs played that game or were at least well aware of it).

UrQuan

Per your suggestion, I'm copying and pasting what I posted in another thread here. This was building off a suggestion from @AshTal to have a prison system.

It would be cool if it worked like this:

If the guards "kill" you they have actually knocked you out, and you wake up in a cell minus all of your stolen goods and gold to pay your bounty.

If the amount of gold taken from you is enough to pay off your bounty entirely, the guard talks to you and lets you go (with a lecture in the dialogue box).

If you weren't carrying enough gold to pay off your bounty, you can wait in the cell until your bounty expires (this represents you completing your prison sentence, and progresses while you're offline in the same way that bounties go down while you're offline currently).

Alternately, you can pick the master lock on the cell door, and go through a heist-like mission to escape the prison while avoiding guards. This puts you in a trespassing area, so if you get spotted you'll get a bounty even if you escape. The prison would be instanced to you and would include both killable and unkillable guards, some with lanterns to detect stealth. There would also be other cells with locked doors (so you can unlock the doors and duck in and out of cells as needed to avoid guards), a locked room with a strongbox holding an amount of gold proportionate to how much gold they took from you (so if you get this strongbox you get back say 75% of what you lost to the guards), and a handful of hiding spots. Maybe 2 different options for an escape route from the building too - one that's through the front door, and one through a different method (maybe a window, maybe a sewer, whatever).

dodgehopper_ESO

I love the idea @UrQuan , Thanks for Posting it!

Benie

The "get thrown in jail" feels like The Ship if you get caught using a murder weapon infront of a guard.
I like UrQuan's idea.