WOW Where do I start? I could give you 10 pages on this subject!
I know a guy who has run his own shop for more then 10 years. He runs around in dirty tee shirts and old jeans, he only buys used machines and spends a lot of time fixing them. But yet he makes a good living and is happy with his lot in life. Then I know people who have nothing but mori & other high end equipment all bought brand new and kept shiny at all times. They run around in Guchi loafers and drive $80'000 cars. It all boils down to who your customers are. Robert Yates would not even see the guy in the tee shirt if you get my drift. As far as the kind of machines you should buy, that is driven by the kind of work you are going to do. I set up a shop to build pistons for NASCAR motor builders. We are talking people who have all the money in the world and don't care what it costs. They just want the very best part they can get and they are willing to pay anything it costs to make it happen. These guys want to hold .0002 on form, size and squareness and they have the equipment to check the parts to make sure they are good. So you have to have the equipment to pull that off. On the other hand I agree that 95 percent of all machine shop work is not that way and lesser equipment works just fine. The old racer said it best "HOW FAST YOU WANT TO GO, HOW MUCH YOU GOT TO SPEND?"
Be carefull what you wish for, you might get it.