I rewrote my first logbook way back when I was looking for my first job and was a bit concerned about the fact that my logbook looked like a rat's nest. Fortunately my old school used stickers as opposed to stamps for logbook certifications, and I had no problem cutting out the entire sticker and gluing it into the new logbook, thus preserving all those priceless signatures of all those flying instructors who are now long gone into the airlines.
I imagine it would be tricky, but you could do something similar with stamps?
I'm onto my 3rd logbook now and it looks even more like a rat's nest, but I'm damned if I'm going to rewrite all that lot! If I was starting again from scratch I'd use a computerised logbook and be done with it.