Phalzyr, more of I was thinking of your respond "limiting how many of those every night options".
I am wondering if may be easier to when it at night to drop down to ask first thing before doing any action:
(After work options)
(1) Meeting Lt. Storm (if selected, then go to which choices)
(2) See John Doe (if selected, then go to which choices)
(3) Go to "The Ring" (if selected, then go to which choices)
(4) Go to "Strip Club" (if selected, then go to which choices)
(5) I'm thirty, should I get Drink (if selected, then go to which choices)
(6) Go to Sleep
That may help reducing the number of listing popping up. It may take a little extra work to start, but it may save time in long run. However I am thinking about it a little more that it may make it a little more complicated. I would have to go through the original game and reprocess my thinking before I provide the recommendation. You are the developer of this project and I am sure you may agree or disagree with me on this.
Otherwise it seems to be smooth method. I believe the originial format is about even in my point of view with your remake.