I realised I did have something suitable on my Glo HD. So, I opened it while reading something on the computer.
First, I just tapped the top right corner, turned the page and repeated. After 37 bookmarks, there was no problems.
Then I went to the first chapter, selected a word and saved a highlight. And repeated for ever second word. After 20+ of these, still no problems.
Then I highlighted a few words in the first line of each paragraph and saved them. About 20 of these with no problems. There were a few accidental annotations in this as I hit the wrong menu item.
Then I started doing actual annotations. This was just select some text, press "Add note" and randomly hit the keyboard. Again no problems.
I now have a sideloaded kepub with 37 bookmarks, 49 highlights and 23 annotations with no errors. I haven't done anything that went across a tag boundary. Though some went across sentences, so there is some crossing of the Kobo spans. I'll do some other tests later, but, at the moment, it doesn't feel like there is a limit to the annotations.
The test book is a novel. The code in it is clean. The paragraphs are just "p" tags with no attributes. For the font I use Georgia with a size about a quarter of the way from the left. The line spacing and margins are at the minimum and the justification is off. The device is Glo HD with firmware 3.19.5761. I don't use any patches.
About the only thing I can think that might be different is that the kepub was probably the result of a conversion rather than a send using the extended driver. I've looked at the results of both and I'd be very surprised if this was a factor.
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