Yes, a good onion routing system should be something like you describe. Especially introducing random delays and dummy traffic to make it more resistant to traffic analysis. Would be nice to have something like that, or alternatives to TOR. How about I2P? Anyone experimented with it? Any other interesting project on these lines?
Back to bouncing basics, sometimes I see people sshing to a box and then from that box they ssh to a second box. This is not proper bouncing. Someone controlling the first box can see everything you do in the second one, can see the password (if you type one), can own the second box hijacking your second ssh session, etc. When you bounce with ssh, you want to build a tunnel to connect from a hop to the next one (-L or -D), and run all ssh clients in your local box connecting through the tunnels.
Another common mistake is to bounce with a single hop. You need at least 2 hops in your bounce chain, so none of them can see both the target and your ip address at the same time. But if you care you would use much longer chains. Then, once you have a quite long chain you would start caring more about traffic analysis.