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It sounds like he has books in ePub format, if they don't work on Kindle. Conversion of those is easy with Calibre.
On the one hand, you said "Now I never tried personally, but could probably find the programs and do it, but that would require me to teach him something that frankly I don't have time for (2 babies at home), and he knows that", and then later you said "if he has to convert it, he can do that", which makes me wonder which is the case: can he convert formats or not?
Depending on where he downloaded the books from, he may be able to re-download them in a different format (the public domain sites, for example).
I seldom turn on the wifi on my iPad, but I play several games on it, so you might want to still consider that, because of being able to use any ebook site on one. They are fairly expensive, though.
Like I said, no straight reader will support both DRM formats, so you are going to have to choose: Adobe or Kindle. I still say that the Kindle environment is the easiest to use, especially if you get a 3G one - no wifi required, assuming that you are in an AT&T coverage area. Sideloading is easy, too, via USB connection.
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