The speed at which he switches hosts implies he's got quite a sophisticated tool chain set up for this. The level of skill really becomes parent if you read the rest of the log though.
There are several minutes of delay in there. I could just about set up a brand new VPS, ssh to it, install irssi and connect within that amount of time. Let alone logging into a system I already had set up.
I agree...
Then the skid chose the nick "root_" in an attempt at appearing to have "rooted" some box...
It's no difficult task to ssh into another server and reconnect, and if "ryan" is who I think it is, he's a bot herder who enjoys DDoS attacks on those who upset his false sense of superiority.
He's well versed in server management, but exploiting other's servers is what he's working towards, and he failed to crack a server belonging to some friends of mine, so his only recourse was a DDoS.
It does not impress me in the slightest bit.