Learning to freehand is always good, but there is no shame in starting with training wheels. I am still of the opinion that the Sharpmaker is the best starting setup that you can have. Yes, you might end up with a selection of your favorite stones but that is really besides the point. The Sharpmaker can teach you two very important things: a) what sharp really means. I have the feeling that a lot of people that start freehanding with no one to help them tend to think that factory edges have been applied with some magic tools that are out of reach for the average Joe Shmoe. The Sharpmaker will teach you that factory edges are in fact usually inferior and that you can do a whole lot better yourself, because, in the end it is quite difficult to beat the Sharpmaker in the end result. Yes it is possible, but when people like Jeff Clark still use a Sharpmaker, it should tell you that there is really no use in letting your pride get in the way of using an excellent system. The Sharpmaker will also teach you that when the edge is set up right, it will take only 10-20 passes per side and no more than 5 minutes to get and keep an edge sharp. If you need more time on a benchstone, you are doing something wrong (that was a very important lesson for me to learn).
The Sharpmaker will not do everything though. It has two very sensible angle setting, but if you want to play around with the geometry of the edge, it is not ideal. Also, the Sharpmaker is not the right tool to hog metal off a blade. The prerequisite to using the angles of the Sharpmaker, is that you start with an edge geometry that is at least as acute, and preferably MORE acute than the settings of the Sharpmaker. If you want to use the 15 deg setting of the Sharpmaker, you should start out preferably with an edge that is 12 deg per side or less. For the 20 deg setting you preferably have and edge geometry of 15 deg or less. Unfortunately, many knifes do not have such an acute geometry coming from the factory. In fact many factory edges are 20++ deg per side. To rebevel them, you need something that will hog metal off fairly quickly. This is were the diamond stones really shine. Ideally, you have an x-coarse DMT benchstone. Unlike the DMT Diasharp stones, the benchstones have a plastic base and are fairly light. You can lean them against the Sharpmaker rods at 15 deg and can rebevel your edges quite quickly (you don't have to take alternating strokes in this step, just take 10 strokes each side, till you have pulled up a burr).
Finally, the finest grit of the Sharpmaker is not as fine as you can go. You can further polish your blades with a strop and some compound. The strop can be anything. MDF board with nothing but compound on it works for example really well. The harder the strop, the more difficult it is to work it and the better result. So a good compromise is a thin legal pad cardboard strop on wood backing or some thin leather on wood (always the smooth leather side, rough leather will work too, but acts like a softer strop). You can go completely wild on the compounds. A good starting point is wax based CrO compound, later you might want to go with some diamond compound. The nice thing about compounds is that they are not a big investment and you add a lot of flexibility to your system by making more strops with all kinds of different compounds.
This system will cost you about $40 for the Sharpmaker (shop around), and about $30 for the DMT. The strop you can get essentially for free, or you can buy one, if you see one that you like. Compounds are usually $5-10.
This system will enable you to get edges that are easily capable to compete with the edges of the best and most experienced sharpeners on the forums. Yes, once you have been bitten by the bug, you might add tools as you go along, but you don't need to. I for example don't like strops anymore. After a few years of playing around, I have found for myself that the best strops out there are the softer type japanese waterstones. They have just the right hardness, you never need to apply compound, they are extremely consistent and they cut very fast at these very fine grits. But it took me literally years to figure out that they really want to be used like strops. No more than 10 passes per side and you don't need to use them to polish. I have been going from 350# or 700# directly to a 10000# stone instead of using a strop and the results are better than I've ever gotten from a strop. BUT would I recommend buying a high quality japanese waterstone instead of a strop? Hell no! The strop will cost you about $10 the waterstone will cost you about $100 and at your current stage you might not even appreciate the difference. Because, while for me the difference my be significant, for someone who just wants a sharp edge, the difference might be rather subtle. So this is something you may or may not want to add further down the road.
The DMT, Sharpmaker+Strop is in my opinion the cheapest system that will give you 100% reliablity and versatility and as I have already hinted at: If you think that $70 total is expensive, then remember that you can spend easily twice to 10 times that for a topshelf sharpening stone and think how much money you have already invested and will continue to invest in knives, which are really no good if they are blunt. The fact that once you are experienced at sharpening you will be able to get a shaving edge on a piece of concrete, the bottom of a mug plus a piece of cardboard is really besides the point.
