I certainly think having a crazy friend to follow you down the long, drunken, dark road of brewing is one of the most important steps. And hey, sometimes you make beer that you're in a hurry to get out of a keg, and someone needs to help.
My AG gear wasn't crazy. My brew buddy already have everything, and I just bought another burner (banjo burner), another 9 gallon pot, another $20 coleman rectangular cooler with a 30" hosebraid and a ball valve on the front. And that was really it. I think having your own grain mill can be really beneficial. We increased our crush a bit, and we finally got our mash efficiency dialed in, and double-milling doesn't seem to hurt.
-Take good notes, ALWAYS!
-Buy grain (and anything, really) in BULK!
-Get your burner dialed in. When I got my banjo burner, I blew through a propane tank in x2 5gallon brews. My buddy gets 6+ brew out of one tank. Yeah, you can hit a boil really quick, but you will waste fuel like crazy. Pay close attention to these things.
-Get a nice thermometer. Nailing your temps really minimizes extra work for you. I have a nice digital thermometer from william sonoma or something. Using a refractometer has proved to be more pain than it's worth. Then again, I also never measure anything pre-boil.
-Get into kegging as quick as possible! I bottled with some friends before I ever got into homebrewing. It totally put me off. So much work. Kegging is so much easier and enjoyable. Granted, you'll end up buying a fridge, but that's another conversation.
I never brewed anything before AG. After getting the basics down with a couple of brews, it's way less intimidating. Good luck, this resource is here for you!