Just a few tweaks/ideas to improve (mostly) the covert quality of life:
Include EAVESDROPPING in the 'see also' section of HELP SNEAK and HELP HIDE. And if there are any other nifty skills like that I don't know about, probably put them in there as well.
Allow people with app 5, charisma, or really high sneak to charm/smooth-talk/sneak past Jalian at the Bluebird.
Why do shopkeepers not trade with hooded folk again? Why is that even a thing? It might be realistic in some cases, but in a lot more its not, and I don't see that it really helps anything.
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Larger ideas (completely jacked from other places I've played recently):
Hire Investigator tail (name): A command to have an NPC, for a large lump sum, follow another PC and report on their location. Players would 'hire investigator (name)' and then after an hour get an echo back "your investigator is in place." They can then do "report" and have echoed back to them the place that PC was at an hour ago. It might be off by a room or two, but generally it would be the area. Doesn't work on locations in Southside. Part of the money paid for the investigator will go to the Thieves guild (like the bounty system). This will do a couple things: enforce theme that Southside is where criminals go to hide, and give your common folk a reason to associate with the brotherhood. This is something that can't be done by players currently because trying to follow somebody with sneak/track so you can report on them is near impossible.
Hire Investigator spy (name): Same as above, mostly, except instead of reporting locations this time the investigator will report the last three message recipients the target sent out to.
You could generally get as invasive with these as you'd like. I don't think people would want this to include house locations though. A general estimate of a certain skill level might be good to include, as that's not generally too invasive, but still has meaning. Perhaps give Brotherhood members a discount on using these commands themselves, as most of them are generally suited to being followed up by sneaking/lockpicking/more PC spy work.
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Honorable mention: Some sort of system where I can toggle my visibility to certain people. I like that characters get bonuses to see my hemotes if I target them, but sometimes that's not enough, especially if that person has especially low wisdom and I have incredibly high sneak. I still hold that, even though it might not be entirely realistic, it would facilitate gameplay by leaps and bounds if I can communicate to my thiefy brothers while hidden in their scene. Also, for those people who want to jerk somebody off under the table, I salute you; this system is for you.
Assorted Suggestions
As a thing that doesn't require discussion, I'd definitely ask you to pop the Eavesdrop suggestion into the typo board, in game, so we can add it.
I don't totally love a tail being completely failsafe, but I feel like some of this might be fixed by the planned changes to hide/sneak (it's not perfect and we are definitely looking into it). If we'd like a tail sort of thing, I would imagine that someone should get a wisdom saving throw to notice that someone is following them/way of shaking them. In all, I don't hate it so much as feel it might be redundant once we fix sneaking, and that it is the sort of thing that would be much cooler if players were habilitated to do it.
I don't totally love a tail being completely failsafe, but I feel like some of this might be fixed by the planned changes to hide/sneak (it's not perfect and we are definitely looking into it). If we'd like a tail sort of thing, I would imagine that someone should get a wisdom saving throw to notice that someone is following them/way of shaking them. In all, I don't hate it so much as feel it might be redundant once we fix sneaking, and that it is the sort of thing that would be much cooler if players were habilitated to do it.
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