Alright. Finally found what was crashing my first server. I was setting these cvars via my plugin, and for some reason that would cause instant crashing when bots join:
So if anyone is still experiencing crashing, try seeing if you have any plugins that use any of those cvars. What this does mean however, is that once again Valve has modified a big part of community servers without putting any information about it in the actual patch notes..
It's not 100% confirmed yet, but as far as I can tell I think they may have removed any possible functionality for renaming/controlling bots. If anyone has a working replay bot let me know, but mine is no longer working properly after this update.