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Well there is only trial and error, and after a lot of that, you can formulate best practice: If you take 100 tall images from books, most of them will be within a certain range (so sort your images into tall, wide and square). If you're captions are shortish, the css above should work for most. If things are different you have to tweak. In general images should not break on ibooks on ipad though, but you can add page-break-inside: avoid; on the img tag as well. Ibooks on OSX on the other hand is not to be trusted with anything
max-height:100%; severely f**** image-dimensions in Adobe Digital Editions. Also max-height, max-width are not support by kindle - it will not break a conversion - for specific kindle productions it is better to do without.
@media is not supported by Adobe Digital Editions. You can do some things with @viewport though to emulate a bit of that - but it is not something I have tested rigorously.
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