One thing to remember is not every lumber yard or mill has a great machine. Around here I haven't found too many mills that sell to the public which leaves a shop that buys everything rough cut. The quality can vary by a lot. I actually like milling my own wood. It's usually pretty repetitive and you see a big difference between the before an after. I like it when I see results. It's kind of like putting primer on a car. Suddenly the car is one color and the lines appear. You know that there's a lot more work ahead but you can really see the wood for the first time.
When it comes to making money things change. Suddenly even small stuff, like having to move tools around because your shop isn't big enough, eats up time. And everyone knows time is money to a business.