Under what conditions does the persuade option become available again?

There's a maximum you can raise a disposition at a time, but I've seen it become available again with time. For some, it seems permanently disabled.

For example, the homeless lady in the Market District. I waited 73 hours and went back in to talk to her and the option is still disabled.

Also, the 3 people needing persuading in the corrupt watchman quest are frustratingly never open to Persuade!

Do you have a mod or tweak that has the deposition permanently stay? I think a Morrowind mod was the same way, I am not sure about Oblivion

I think it has to do with the Fame/Infamy ratio.

Edit: And maybe your Speechcraft skill. I'd try bribing, if the price isn't too ridiculous.

When your Fame gets high enough, everyone starts to love you, and Speechcraft becomes more or less completely useless, since the game will only allow you to persuade them so far.

All in all, the implementation of Speechcraft in this game was abhorrent at best. Don't feel bad about it, it wasn't your fault.

Just be glad there is no context-sensitive dialogue attached to the skill anywhere in the game.

This is absolutely true.

I ended up taking Speechcraft as a major to slow down my leveling speed because it's so useless.

Even with apprentice Speechcraft, I found you will be successful talking them up to around 65-70 and then giving them a few coins to "befriend" them that bit further.

I don't know why you can't initiate the persuasion wheel though, OP. Sorry :sadvaultboy: