I think the key is whether the "shifting" is done for private and non commercial use. If you buy a product (a book) and convert it to ebook and NOT uploading it and sharing it, you are doing it for private and noncommercial use. The seminal case on this issue is the Sony v. Universal Studios case from 1984.
The Copyright Act grants the copyright holder “exclusive” rights to use and to authorize the use of his work in five qualified ways, including reproduction of the copyrighted work in copies. I think you may be entitled to argue that there is no "reproduction" by converting the book from a paper to a ecopy so long as the paper copy is destroyed or not sold. After all, you are then left with only one copy.
The key points to that case include
a) Sony presented testimony from other major producers who indicated that the recording of shows was not unwanted.
b) The equitable rule of reason was applied to ascertain "the commercial or nonprofit character of an activity" and "the effect of the use upon the potential market for or value of the copyrighted work"
The purpose of the copyright is to provide incentive for "creative effort." By allowing a format shifting for private, non commerical use would not impair incentive for "creative effort" so long as the first copy was legitimately purchased.
Considering this language in conjunction with the right of resale (the first sale rule), it doesn't seem likely a court would find that format shifting is one that would find favor with the courts.
Frankly, given how sue happy RIAA is, if they thought they had a leg to stand on, companies like this
one which promises to convert your existing cd collection into mp3s would be in court right now.
Further, if you read the copyright page of a book, it states that the it is a violation of the copyright to scan, upload and share not just scan.
Finally, I disagree that the DMCA would apply. I think that calliing a paper book an "analog" copy is a distortion of the meaning of analog as it is generally understood.