I find myself needing to reset two NPCs in the game. Is that possible?

In one case, Leondric, the guard in front of Penumbra's prison, doesn't go away after I talk to him. However I restored an older save from before my first conversation with him and it seems that if he's the one who initiates the conversation with you and you go through all dialog choices, he does go away... if you talk to him again later it no longer works. So basically I blew my only chance of getting him to leave because I didn't do it during our first conversation and I would like to reset him so HE would start talking to me instead, like the first time.

In the other case, I was messing around with the wishing well and ended up overwriting a save and being stuck with the wishing well telling me to go to hell and me getting nothing. Reloading an older save wasn't an option because that was too far back...

You might need to move away and then go back to rescue Penumbra. In my game I couldn't get him to leave, so whet into one of the other side rooms nearby, figuring I would continue looting and check back later; he followed me in after a short delay, and I could go let Penumbra out.

There is probably a way to get the wishing well to offer another wish, but it would be easier to just use iZakaroN's SaveEditor (or from Kiya's site, with description) to give yourself the reward you wanted (see the Wishing Well (Spoiler)). The topic Wisdom - is it worth the skill points? gives the formula to determine how many experience points you would need to reach the next level, if that would have been your wish.

Thanks for the help!
I'm not having any luck with Leondric... he's not moving at all. When I played my old save and it worked, it happened as a cut scene and I had to wait until it was over... I don't think it would happen any other way, he wouldn't just start wandering around by himself? So the cut scene has to be triggered somehow...

As for the wishing well, that was my own mistake so I can live without it but I do want to get Leondric to leave so I can solve the quest without killing anyone.

Did you use the conversation option "you seem nervous friend...", finish the conversation and then head back trough the door to the west? That should get him to move to the room to the south.
I forgot part of what happened; he did 'follow' after me to the room in the south, but only once I headed back to the hallway to the main part of the guild.

Yes I did, I used all possible conversation choices as well as just the "you seem nervous friend..." option and exited to the west but nothing :/

I also tried hanging around in the south room and after a while leaving for the west room but no luck.

What happens if you click on the door?

If I just look at the locked door, Leondric starts attacking.
If you meant the west door, I tried closing it from outside and inside and going through the same process with Leondric but nothing happens differently...

I did mean the north door. I know you were looking for a non-violent solution to get rid of Leondric, but since there was an issue with him walking away, I was curious if he would react normally to clicking on the door.

If you really don't want to kill him (in self defence; there is no loss of reputation, or reaction from the rest of the thieves), something like the technique in the FIX for broken Imp Council Member quest topic may help. See the fix topic for details, but basically you could try making a new save by the west door, in the save folder backup the dialogs.000 file and 2 story.* files, copy the corresponding files from an earlier (or new) save, reload the save by the door and approach Leondric, go through the conversation options (particularly the nervous comment where you mention rats) and then head back trough the west door. If he leaves, save the game in the hallway, copy the original dialog and story files from the save by the door into the new save in the hall, overwriting the versions there, then reload the hall save and go open the north door to let Penumbra out.

That worked! Everything went as it should be with with one oddity- after Leondric left, unlocking the door with either the key or lockpicking immediately locks the door again for some reason... after the door locks again, only the key opened it, level 5 picklock didn't even help. What worked for me was to try and picklock the door first with lvl3, fail because my level was too low, use the key once... and somehow that worked.

I actually used your fix for Mardaneus a little earlier (thanks a bunch for that, it worked) and I did try to do the same thing with Leondric but I only copied dialogs.000 and nothing else.

Thanks for your patience, I can finally go on with that quest now...

Glad you got it working. Part of that quest (tracked in the story files) may have been updated early, or something. I wasn't sure if replacing the dialog file would be necessary, but the story files would be in order to hopefully reset the cutscene conversation as you approach.

You restored the dialog/story files and reloaded before trying to lockpick the door? Maybe because the original version was not updated with Leondric leaving, part of the game didn't want to let you in. If may have worked better had you opened the door first, then saved and replaced the original files, and reloaded before talking to Penumbra.

BTW, you can get a level of Lockpick in the thieves guild if you loose a bet / challenge.

Yes, I already lost the bet. I can get my lockpick skills up to 5 depending on what equipment I have on...