Revisiting the Backlist

I've been giving a lot of thought to my backlist lately, books and series that have been out there for a little while. There are quite a few of them that I could get the rights back to and re-release on my own. And I'm tempted--so, so tempted.

There's the prospect of new covers--something that's always a treat. Even when I initially loved the original covers, who doesn't like a makeover? And in those rare instances where I wasn't completely over-the-moon about a particular cover? Yeah, then it gets really exciting.

There's the lure of total creative control. Including picking the aforementioned covers! I can also price the books any way I want, give away as many copies as I please, and re-edit them to my tweaky little heart's content.

I'd get to keep more of the money. Really, I can't find a problem with that part. Not. At. All.

Finally, and perhaps best of all, I'd have the excitement of release day, several times over, all over again. I'd be introducing new readers to books and worlds I've loved creating and reminiscing with not-so-new readers...

But those are all in the "pro" column. There's a "con" list as well.

It takes time to do everything that's required to relaunch close to two dozen books. And yes, I could start with a few and see how it goes, but that would just mean spreading the pain out over a longer period of time, rather than eliminating it.

Of course, I could hire someone to help me with everything that needs to be done.  In fact, I absolutely would be hiring several someones anyway--an editor or two, an artist, possibly a formatter--but that would still leave me with a lot of tasks, big and small, and when it comes to self-publishing, the buck stops here.

And all the time that I'd be spending revising all these older books is time I would not be spending writing new books.

The biggest challenge--the stumbling block that continues to keep this process on hold for me--is the question of whether or not (or how much) to update the books. There have been a lot of changes in the world since some of the older books first came out. Politics. Technology. Trends in fashion and entertainment that have come and gone.

So here are my questions. And I'd love to hear your thoughts.  

How critical is it to you that a book appear to be "current" in all aspects?  And, if you'd read and loved a series in the past, how disappointed would you be (or would you not be disappointed at all?) if said series were to be re-released with significant changes?