Well - it appears my little batch file doesn't detect this crashing...
Atleast I just acknowledge the error and it boots up straight away now, no longer using the Steam Client itself to run servers but the hlds tool. I've started up #1 for now, but I'll boot up #2 in a little while.
So that way, #1 crashes - jump onto #2.
I'm also running devicenull's metamod, to block a couple of items (hopefully the default install of it works fine)
That offer is still there to host a 1.9 server :-)