Ok, so I do have WebOS 2.1! Great! lol. All I did was download WebOS QI and ran the jar file. Here is the link:
WebOS Quick Install v4.03 - PreCentral Forums I ran it and it just worked. I made sure my phone was plugged in as "just charging" I ran it on a Mac and WebOS doctor for 2.1 was in the same directory as WebOS QI (although I don't think it matters). Try running it with the phone plugged in and make sure you have the latest version! I don't think the old ones work with WebOS 2.1