We jumped in with both feet. I live in Ireland and run a business in the U.S. tied to the home housing market. Needless to say, like the housing market, it is just about dead. So we wanted to stay in Ireland and needed to make euros so decided to stop talking about becoming coffee roasters and 'just do it'. Thankfully my wife, The Lovely & Talented Roast Mistress, was able to ramp up her skills rather quickly (thanks for giving us the confidence that we could do it Duane!) and is turning out coffee that is getting great reviews.
Now it is all about the business end of things, managing cash flow, chasing down late payers (which can be a full time job so factor that in when thinking about starting to roast), finding good suppliers, constantly tweaking our labels, being smart about taking on new business (i.e. I can't drive 50 miles with gas at $8.50/gallon, deliver 30 bags of coffee, and expect to make a profit unless I'm delivering to several people along the way), and growing as fast as we can without taking on any debt.
As to labels, even though it has been a gigantic pain I'd recommend printing your own to begin with -- if they have any amount of complexity. For us we've made lots of tweaks to both the front and back labels of our different coffees, usually at customer's suggestions. I must say, there have been several good ones.
After printing several thousand on our own I'd say we're getting close to 'being there'. If things stay static for the next few thousand labels then we'll have someone print them. The last thing you need is boxes full of labels you wish were different.
Of course if you aren't selling where the labels have to have a lot of info like ours do, then something plain will make your life simple. I think Duane uses a big rubber stamp on a kraft bag. Looks good. Really simple. Low cost.
Well, enough about labels. Watch out for EPA emission regs in the U.S., having to add an afterburner to your roaster can be a killer (from what I've heard, thankfully I don't have that problem in rural Ireland).