Ahh, this may be the final update!

I had lunch with my friend. She confirmed most of what I suspected and shared some stories that scared me off even more. The company, including the owners, thinks that IT is just a cost center. They think that IT people just make up stuff to do to keep themselves employed. They would rather lose hundreds of thousands a year in stolen equipment, unmanaged contracts, and insane purchasing practices (never mind their exposure to data theft!). They don't get it.

Also, even as a contractor, I would be reporting to this guy.

I told my friend that I'll work directly for her, but not for him. She has some projects she wants me to do, so at least I will keep my hand in it.

Also, I heard from him this afternoon, asking if I can come in Friday and suggesting we wait until after the new year to pick this up again if not.

So now I have to decide whether to tell him that I am not interested now or drag this out further. I also have to decide whether or not I want to suggest a contract arrangement to him for project based work. I just have such a bad feeling about reporting to him.