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Have you tried to copy/paste instead of using the selecting method?
Yep, totally works. To clarify, copy and paste 5, then multitask and do it again. I just sent myself an email with 9 pictures doing this. If your on an iDevice that doesn't multitask you should be able to save as draft and go back and forth.

[EDIT] Works with videos too as I just sent myself 8 videos. At 2 seconds each it still took a while.
 
Too much work, i just wanted the limitation gone when i select multiple images/videos to send. :S
 
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