Imo the radiant quests of the Thieves Guild are repetitive. Extremely repetitive along with being unchallenging. I'd rather have individual quests in the Guild that involve actual thievery (you know breaking into a mansion and having to sneak past guards and stuff basically Thief style) and proceed to get more difficult and complex (you'd have to abide by specific rules if you want to get bonuses such as not killing guards or being seen) as you go on. Instead we get these boring radiant quests. >_>
P.S. I wish burglary and home invasion was as easy in real life as it is in Skyrim. Seriously, I'd be a millionare.
I'm glad you brought this up.
"Sneaking" in general is something that needs to be, as Christina Norman at Bioware would say "High-Risk, High-Reward", in that it sets you up for lopsided or extreme payoff, but it is also very hard to pull off.
For starters, if anyone not a "Friend" in town, or a guard, sees you sneaking, at the
Very Least the Guard(s) need to interject with a warning, and
Then follow you around to make sure you're not going to cause trouble. They won't arrest you until you actually break the law (Sneaking isn't a crime), but it makes playing a "Sneak" Character a bit more tactical, having to anolyze surroundings and note patrol routes. More importantly, it also gives a level of necessity to Nighttime action.
What's odd, is that this is actually already possible in-game. The Thalmor Khajiit assassin in Riften behaves
exactly like an alerted guard should. But instead, stealth remains an immersion-facturing "I win" button.