baran3,
I have some recent experience that may provide a bit of information. I recently got into the wire edm business (about 15 months ago).
I've been a machinist my entire life, typically specializing in very precise parts and/or things others didn't want to do. Computer/CAD work has also been a fairly obsessive hobby for many years. This "base" of experience made the transition easier (I didn't say "easy"... only "easier").
I also had a very experienced wire edm person take me "under his wing" for a while which put me way down the road on the learning curve.
My plan was to buy a used wire machine and basically be in the position where I didn't "need" to make any money with it for a good while. I did my first paying job about 3 days after the machine was hooked up in my shop (someone overheard me at lunch talking to a friend about my wire machine).
Essentially though; I have not pursued work (yet). Work has come to me simply through word of mouth so far. Once again though; I have/had an existing machining business with a good client base that kept the money coming in while I was picking up experience. Pretty much all the money I made in the first year got put right back into more and more tooling, a hole popper, spare parts, wire, filters, resin, and a LOT of practice.
As far as lower tooling costs and running unattended:
Have you priced System 3R tooling? It is hyper-expensive compared to tooling any other type of CNC equipment.
Running unattended is a great concept... and one of the reasons I got into the business as well. However... it doesn't really work that way (or let's say; hasn't for me). A good part of my work is coming from a very high-end aerospace firm that has a couple of wire machines of their own. They send me overflow... and typically that means work that is too finicky, requires too much attention, and has to be too accurate for what they want to do in-house (not to mention the parts are typically fairly low volume). They keep pretty much all the more production oriented work (that runs unattended) for their own machines, and farm out the time killer jobs. I don't blame them -- I would do exactly the same if I was in that position.
The bad part about picking up work that way is that it's time-consuming, intensive, not-very-profitable work.
The good part about it is that you gain a tremendous amount of experience in a short period of time.
So to answer your question (or at least attempt to): I think it would be quite difficult to start out "cold turkey" with a wire machine and make a living. If you have other means of support (and it sounds as if you do), then it's a very interesting, fun technology to get into. The kind of work you get will be somewhat dependent on the kind of connections you may already have in other fields of manufacturing/machining.
If you have more specific questions, fire away and I'll do my best to answer.