Don't worry, you are not alone in having issues with damp braiding. I cannot manipulate my hair much (bunning/braiding) when it is wet.
If I wish to wear my hair up, then I have to make sure that it is *completely* (I cannot stress that enough) before I put it up. Otherwise I end up with kinked, damaged-looking ends.
However, you also mentioned that you have past damage and it could also be that your ends are getting more worn out as they grow longer. Since you pointed out that there may be more than 1 factor involved, you may want to observe if you encounter the same problem when you next damp braid your hair.