As per your request, here’s how it worked out —

Here is a screen shot of what I did in the end.
I tried out all the ideas given here and in the end decided that Anne-Marie’s worked best for me.
https://www.dropbox.com/s/u3pvbchegj9bz9i/joke-book-layout.png?dl=0

The book included:
Riddles with answers
One liners
Facts related to the joke being spoken by the book series’ mascot
Longer story-type jokes

I also added a separator between consecutive riddles with answers which were made of up a hand-drawn emoji type font with a rule behind it.
The one liners and stories have line above/after to separate them.

The client provided the file as a Google Sheet.
Since the majority of the jokes were riddles with answers, I brought in just the first column of text to get one long file of jokes/riddles.

I used search/replace to replace every end of paragraph with 3 end of paragraphs.

I then selected all the text and applies my “joke” style and the next style to create the pattern of joke, answer line (a blank line with the correct spacing to accommodate the anchored text box of the answer), and divider.

Then I brought in the answer column and used the script Anne-Marie noted to split each one into its own text box. I flipped them and shift-dragged them into the empty lines that were waiting for them.

As I went along, I changed the style on the one-lines and stories and deleted the extra spaces after them.

When that was done, I added int he blurbs manually. I had the character in 4 different positions and had them sitting in a library. I dragged one out, switched the text, and anchored them into place with their own par style to ensure correct spacing above and below.

Finally, I went through the dividers and inserted letters at random – each one a different face. I originally set this up as a numbered list with letters and while it worked great, I didn’t like all of the faces so I wanted to stick to specific keys.

The book has over 350 jokes and I was able to do all this in about 4 hours.

I hope this helps someone.
Thanks again all for your help. It was fun to figure this out.

How creative. I am playing around with this to see how easy it is to match the sample layout I have made for a regular text layout.

What I have right now is:
one liners
riddles with answers on the following line, upside-down
interesting facts about some of the riddles in a speech bubble being “spoken” by a comic figure

Between each of the answers and the next riddle (that is, when the answer is not followed by a one liner which has its own style and font) I have a dingbat with a line as a separator.

I can’t really auto-format this even with “next paragraph” styles because there is no pattern.
I’ve set up shortcuts on my styles so it goes pretty smoothly. As the majority of the jokes are with answers, I do have a next style built in and just adjust when necessary. The most time consuming part is flipping and inserting the upside-down answers.
Now I’m trying to figure out how much of a time saver the table will be with the variables mentioned above.
I made a cell style for each kind of line but applying them feels more time consuming than regular style application (unless there is something I am missing here).

Thanks so much for weighing in. It’s great to have a forum of helpful people!

@David, are you suggesting there is a script that could be written to flip the answer boxes so they don’t have to each be done individually?

Thanks for the advice and the chuckle :)
I’m somehow thinking this joke book mght be just up your alley….

Todah!

Its 16. I could do that :)
I just thought maybe there was an easier/faster way.

David – that didn’t work. It found the last 3 digits for things like 6,000. But didn’t find any footnote references. I’d love to understand why.

Dieter – thank you! That worked like a charm!

A lot of the workflow I learned from you and your advice over the past decade :)

The resave did the trick. Thank you!
Now I think I recall having this once before.
Must remember this for the future. Seems odd, but if it works, that’s great!

Thanks again!