Join Date: Apr 2010
Location: Near Boston, Massachusetts
Lots of good advice here. Here's my take, which is similar.
For your first plane, buy something new and reasonably high quality. You don't want to mess around with trying to figure out how to make it work when you don't actually KNOW how it's supposed to work. "Reasonably high quality" doesn't mean you have to go out and spend $500. One way to do it is to go out and buy a bunch of planes, but that's expensive, and you might not know what you need.
If you're looking to dimension, joint, and smooth, you can arguably do that with one plane, with some limitations. If you buy a decent #5 -- WoodRiver at Woodcraft has been getting reasonable reviews -- it can joint and smooth small boards, maybe up to a couple feet long. Jointing takes practice, but as a general rule I've heard it claimed you can joint a board twice as long as your plane. The stock blade will take care of jointing and smoothing, with slightly different setups.
For making boards thinner, or bringing "rough cut" to "workable but needs smoothing", you may want to invest in a second iron. For removing lots of wood, a radiused blade and a wide open plane mouth is the traditional answer. So you can buy a second iron for your #5. If you can, buy one pre-radiused. That's easier than doing it yourself. If you can't, then get a grinder and very carefully grind it down. You want maybe an 8" radius, something like that.
There are limitations to this approach. For one, you'll need to reconfigure the plane every time you want to switch tasks, which is annoying. For another, a #5 is really a little bit short to be a jointer, and is oversized for smoothing small boards.
Over time, though, you'll figure out what you want. My three most commonly used planes are an old Stanley #3 smoother (I have a 4, but I don't like it as much), a Stanley #5 jack which mostly gets used with a shooting board, and an old 24" long transitional jointer which was probably made by Seigley. At least, that's who stamped the blade.
Once you're comfortable with those, you'll find yourself looking for moulding planes (plows, rabbets, and weirder stuff), but you don't need to think about them right now.