I think it sounds like a great deal! :-) I'm going to work summer school so I can get a Bailey, too.
What frame does it have?

If you are saving $1400 jump on it before anybody else does. I have the same set up and my learning curve was not as huge as I expected. I have always had mechanical machines and I like the ease of maintenance. Just one tip, this is a good, solid, workhorse, but it is not über fast, so no sprint quilting :). Good luck, you are going to love it. You can modify the handles for under $5 bucks with PVC parts from Home Depot. Good luck!

Chuck just LOVES to talk and he is very happy to help anyone with one of his machines. When I was there, he said he often helps folks resolve machine issues right over the phone so they don't have to ship it to him. He is genuine and gives great customer service. I sort of joked with him [since he's a bit older] on who would be that knowledgeable when he can no longer service his machines. He says that his sons are learning the biz, so no worries. :)

One nice thing about buying a Bailey from the original owner is that you can contact her if you have any questions or need advice, etc. Bailey has a very nice forum and it has a lot of good information addressing a lot of topics.