Its not as complicated as it sounds. You shouldn't have someone do it for you. When messing with the phone like this, you run the danger of your phone messing up. At that point, you need to know what to do and not rely on someone to come to your house and fix it. Rooting your phone is as simple as downloading an app and pushing one button. I think you can manage that.
Speaking as a very inexperienced user ut is quite easy to root and flash once you read the instructions and like a post above said if you do it yourself that way you get the experience to learn how your phone functions.
Yea, you can definitely do it yourself (although I will be more than glad to help if I can)
It takes about 30 seconds to root using one of the one click root programs. Gingerbread is a little more complicated, but if you can rebuild your harley (& I know you can do that) you can certainly figure it out.
I ran the gingerbread leak for a few days & didn't particularly like it & went back to 2.2
I rooted and installed custom roms on mine and my bf's DX's. Its easy peasy. The worst thing the you can do is brick your phone, which can be fixed. Read up on it, try it out. If you need help a long the way there are some pretty awesome people here who can help you out. I was scared at first, but I got through it.