Old thread, but I'll play along.
Calibration would be a must for the OP. He's sending stuff out to be printed and not getting the results he wants. Color calibration will solve that. As a professional printer, I have to deal with this all the time from photographers. Every time a photographer (and to a lesser extend, some graphic designers) send me something to print and the proof doesn't come out like they think it should, they blame me. And they always tell me it looks fine on their screen and for some reason, they usually say something about it being a Mac. Apparently there are people out there who think Macs are self calibrating. Then I have to tell them that we've spent tens of thousands of dollars on color calibration software and hardware alone, and that all of our equipment is calibrated as well as it can be calibrated and constantly recalibrated. Then I tell them that on my calibrated monitor, their photos or designs look just like the proof. Then they ask me what settings they need to use on their monitor for next time, and I tell them to get a color calibration system, because you can't just blindly apply settings and expect to get something that works. They say those are expensive and they'll think about it. Then they send me a new job about a month to a year later, and we go through the entire process again, because they learned nothing and still assume that color calibration isn't really necessary.
However, if you're just printing at home and you're not too picky about your colors, you could just adjust your monitor to look like your prints, and go with that. Calibrating stuff by eye works well enough for some people. And in the controlled environment of your home, you could probably get away with it. But if you're going to send your work out, and expect it to look the same on your monitor as it does on every other monitor, and if you expect your prints to look like your digital files, then actual color calibration is a must.
And that's the whole point of a professional color calibration system. It's not there to get you the best results possible. It's there to make sure everyone else gets the best results possible, just like you.