I created a windows service that monitors the CS Server and will restart it if it crashes. Since I use a batch file that randomizes the first map selection, there should no longer be any issues with the server being down more than 10 seconds.
Had to reduce the bots by 2 because the server ran into the Edicts limit on de_dust_go (too many entities). If it happens again, I'll reduce the bot count again. Until it is resolved.