Assuming you installed with the Kick-Start CD, the updates are automatic. At each bootup it does an apt-get update / dist-upgrade, which upgrades to the latest version. You can see and modify what gets done at bootup in the Pluto Admin site under Advanced, Boot Sequence.
I have to defer to someone else about the networking issue.
Regarding the Orbiter, this should work. Each build includes a version for Windows, Windows CE, Linux and Symbian. Orbiter has been quite stable--we were running all 4 versions at Cebit. Although it's true you can't use the 18.104.22.168 Orbiter with a new DCERouter.
Go to your pluto admin web site, on wizard / orbiters, confirm that you have added an orbiter already. These would have been pulled from the installation wizard at plutohome.com. If you recently added the Orbiter and haven't yet rebooted, it's graphical images won't have been generated yet. there's a program "OrbiterGen" that pre-renders all the graphics and determines the correct screen layout for your type of orbiter, screen resolution, aspect ratio and so on. At bootup on the core, this gets run for all the oribters.
Or, faster than rebooting, you can also go to any other orbiter, click the pluto logo in the lower left to bring up the advanced page, and choose 'regen all orbiters'.
Now, from the main login page (the start page) of pluto admin, click the link to download orbiter win installer. From that next page, choose the windows xp/2000 version (or CE), and it will install the software.
I just tried this myself since the installer is new to version .12. The only thing that didn't work right was that it didn't ask me for the device id of the orbiter, and the ip address of the router -- the 2 pieces of info needed for it to run. When I ran it from the shortcut, therefore, the orbiter failed to connect to the router. But it did work when I ran it manually from a command prompt, with 'start' 'run' and then:
"c:\Program Files\pluto\Orbiter\orbiter.exe" -d 7900 -r 10.2.1.165
7900 was the device id from my orbiter, as shown on the Wizard,Devices,Orbiters page, and 10.2.1.165 was the IP address of my core.
Let me know if that works for you.