The Spyderco Sharpmaker 204 is easily the most reccomended sharpnening system on the knife forums. At $50, it might seem a tad "pricy", but it won't break the bank. It's easily comparable to the Gatco, Lansky, etc systems in terms of price (actually cheaper in many cases). But it's far easier to use. And if you consider the cost of the sharpener versus sending the knife back to the factory (usually under $5, or free, plus shipping costs), or paying someone to do it (like a knife shop), it pays for itself pretty easily. And it's certainly more convenient.
About the only sharpening system that gets better reviews is the Edge Pro, but we're talking 3X the cost.
IMO, the best way to sharpen knives would be learning with a system like the Edge Pro or Sharpmaker, then freehanding for touch-ups and maintainance. Personally, I reprofile with the Sharpmaker (I also have the diamond rods), but other than that, 99% of the sharpening I do is freehand with the Sharpmaker rods, or round ceramic rods that I pulled from a "ghetto" Sharpmaker with a wooden base. I learned sharpening freehand long before I used a system, and I'm better for it. However, this includes many ruined (thankfully inexpensive) practice knives. But the Sharpmaker system helps a lot for heavy work. I'm heavily considering an Edgepro though.
For the price, the Sharpmaker 204 can't be beat. Chances are that even with practice, your edges won't look factory perfect. You'd probably need an Edgepro for that. But if it cuts, what does it matter? All my edges will pop hairs, but none look factory.
In the end, you've got a $350 knife. $50 to maintain it is very reasonable. You wouldn't buy a Ferrari and feed it regular 85 octane gas, right? And chances are that you have more than one knife. Most of us have several, doezens, or even hundereds. I myself have spent over $5000 in knives in the past year or so. I have the full-kilted Sharpmaker setup (standard kit, plus diamond and ultra-fine rods). About $110. Plus I'm thinking of getting an Edgepro. $300 for sharpening equipment sounds like a lot, but not compared to the $5000 in knives it'll be maintaining.