This topic hasn't gotten a post in the last seven months, so I thought I'd share some of my conclusions after living with my iPad since last July (2013).
Regarding loading comic book scans onto the iPad, I eventually realized (in a real 'duh' moment) that it was way easier to just access the Preview feature at DCM for any comic in the archive and read it that way. No need to load scan files into my iPad's flash drive via Dropbox, iTunes, or any other route. Now, that does mean that I have to have wifi access, so if I am on a plane flight and they don't have wifi or do have it but charge $ for it which I don't care to shell out, I'm stuck with just what I have on my iPad. But I take maybe two or three flights a year, and I can always read the free ebooks/pdfs I have loaded on it (Complete Sherlock Holmes is a good one).
So, for me the whole uploading scans thing has become a non-issue.
I will say as a footnote, that I've been fairly underwhelmed by my iPad. I don't play video games or watch movies or update Facebook or most of that stuff, so I keep asking myself "exactly, why did I need this?" It is good for checking out sports stats and facts while watching a game on TV, I will grant you that. But once this iPad has crept into obsolescence, I don't really see myself replacing it with a newer one, unless they totally revolutionize it in some manner.