I am very close to "sisters" to you on your story. I had the "walmart" singer at first, then I caught the bug in October!
I will ONLY buy used machines, and am very very very satisfied with my pawn shop Janome.
I have also had (in no particular order) the following machines since October: 1972 Elna, 1964 Kenmore 48 (lavender! so cute!), 1954 Singer 99k, Juki 98e, Janome l-392, (2) Singer Simples and another Kenmore that I can't remember what it is!! I am also waiting on a part for my Singer 7422. It is certainly not vintage! Oh, I see you are in Middle TN, would you like to buy a Singer 7422?
In my many months of looking, I've never seen a used BabyLock, though, so that might be a sign that once you have one, you never get rid of it!
I am so tight that I squeak when I walk, so I have a hard time parting with $20 for a sewing machine, much less $500 for one. My husband bought me the Juki with a frame set-up for $750 and the whole time it was in my house, I felt guilty and didn't want to use it at all. I finished one quilt on the machine (off-frame, never did get the hang of it) and sold it and felt much less stress.
Also, I have learned to take the tupperware off the machine, clean it, oil it, tinker with it and put it back together. I would NEVER attempt this with a machine I had a huge investment in. Yes, I realize if I spent $400 at the dealer, I could take it to them and drop it off and wait a week or a month for them to do it for me. But I don't have time for that anyway. I live in the middle of nowhere and I quilt like other people (normal?!) watch TV. I love my machines because I don't have to worry about them or baby them.
I have compared buying a sewing machine to buying a car too (I have a Camry too and it's barely broken in with 225k miles!!) and it's almost exactly like buying a motorcycle. When we started riding, we started with small bikes and traded until we got exactly what fit us personally. I've done the same with sewing machines. I started small and found out that I liked playing with fabric. I got a small starter machine then tried different ones that I acquired. I know it sounds like I've spent more than $500 on these machines, but I've kept a very careful record and the bottom line on what I've bought and sold is $210. I still have four machines, and I need to part with three of them, so I anticipate "sewing for free" soon! I am going to try to attach what I have left.
It is a totally personal choice, but I am the type of person that tries to buy *everything* used for my personal economy and for the environment. I also enjoy the thrill of the hunt and the anticipation of the sale, which isn't for everybody! My husband and I both love going to estate sales (bad place to buy machines!) and antique stores, pawn shops, thrift stores (another bad place!), etc and I cruise Craigslist daily. He has his "collections" and I have mine! For us, it's a no-brainer. Our hobbies are self-sufficient at this time, and as long as it continues to be, I don't have to wait for a windfall for my dream machine! I just have to be at the right place at the right time!