Some say yes, that technology and attitudes have changed. (Some of these authors involved in the discussion have books from the 1980s and 1990s.) They say that readers will be jerked out of the story if someone is looking for a pay phone for example.
I totally understand wanting to do this. There's an unfortunate reference to MySpace in one of my books that was written before it was obvious it was in its death throes. I'd love to erase that, but this is a book to which I do not have my rights returned.
Other authors on the loop say, no, just put the year it was published at the front of the book so that readers realize when it takes place. They ask an interesting question: If a book is updated now, will it need to be updated again in another ten years because of technology changes?
There's also a debate about early books not being as well written versus early books having a certain something to them that comes from that inexperience.
What's the most interesting to me, though, is this is a debate I had with myself a few years back when I got the rights back to four books and a novella. The earliest was only written in 2002, so it was less than ten years old at that point, but my writing had improved and I write much tighter now than I did in my early work.
I ultimately decided not to rewrite, but to correct a few minor things that either were introduced in edits or that had always bothered me. There were many reasons why I opted to do it this way.
First, if I rewrote--especially my first story--what I released would bear almost no resemblance to the originally published version. It would (in essence) be a brand new book and there were too many readers who wanted an ebook version to spring a completely different story on them.
Second, the time factor. I'm a slow writer and I'm even slower now that my day job hours and commute time in Georgia have stolen two hours from each weekday that I used to have when I lived in Minnesota. I wanted to spend the time I did have to write on new stories.
Third, all four books and the novella were set in the future and all of them were written in the 2000s. I simply didn't have the kinds of issues to deal with that authors who wrote contemporary romance in the 1980s have to consider for a re-release.