No, no private punishment days were left. I never really needed them except when getting punished was unavoidable.
My sneak and persuasion are really high so I do not get caught peeping often, and when I do I just reload so it never happened. Also, by the time the private punishments unlock most of the things that would get you punished before no longer will, no need to peep when you can just walk in and get a hand job or blow job.
I share your frustration with vauge information. It seems all the walkthroughs for this game on the entire internet are right here in this thread, and they are not exactly detailed or complete.
I only had them because I was using a money cheat and paying Mom for private punishments was a way to keep her mood high. I'd pay her 1000 every day or so, so I maxed it out pretty quick. Didn't know it would fuck me in the long run.
Lisa handcuff punishment: you can spank her or get a blowjob as far as I know. Maybe that's where the handcuffed and anal with Lisa happens that you mentioned, but I never got that one. You can also handcuff her to the bed during "Play with Lisa" at midnight. And occasionally, you'll wake up handcuffed to the bed by Lisa in the middle of the night.
Changing Roles starts when running Blog and Arachnophobia. I don't remember exactly when, but it will be obvious as Alice will pull both of you aside and lay down the law. Just follow the progression from there.
Hot Coffee: apparently, you can get to the point that Lisa tells you about the bartending lessons, but it's not actually in the game yet. I imagine if it were, it would be under the Online Courses tab on the laptop, but just locked until it was available. Pretty much the same way the Erotic Massage course is on the laptop from day one, but you can't actually take it until Kira tells you about it.
Yeah. Not only is the information vague, but I've seen some people on here who seem to get annoyed if you ask questions. At least I've found a few nice, helpful people to share information and tips with.