Does pilpbox run on a proper Ethernet TCP/IP stack?
Yes, Plipbox is the way to go for you. It runs great with A1000. If it comes to TCP/IP stack then I recommend RoadShow. It's fast and lightweight. With V500 you should get around 100 - 120 KB/s over LAN/FTP.
Just one thing to remember A1000 has got a bit different parallel port than all the other Amigas.