Join Date: Apr 2010
Location: Near Boston, Massachusetts
My views on this are non-conventional, and reflect my own personal experience rather than anything else. Here's my advice, on the assumption that you have few or no power tools. If you own a powered jointer (or are comfortable jointing on your table saw or router table), skip the first step.
1) Start with a jointer. Jointing is (relatively) easy to learn if you have a long plane. You might find it helps to clamp something to the plane to use as a fence. Why start here? Because learning to tune a smoothing plane sucks, and if you don't know what it's supposed to feel like you'll just wind up frustrated and with a lot of nasty plane tracks. A jointer is used for making longish boards have one straight edge, which you'll need to do sooner or later. Start out using sandpaper to get things smooth.
2) Add a jack (Stanley #5 or equivalent). Removing lots of wood from a board is much easier if you have a jack, and again, they're not as fiddly to set up as a smoothing plane is. But you can use it to get a pretty smooth surface if you work at it a little bit.
3) Get a rebate plane. A Stanley #78 or equivalent is a reasonable place to start, since it simplifies the process somewhat. Cutting rabbets is annoying without one, and trivial with. Just don't ever trust the depth stop, and learn the quirks of the fence on yours. I've used three, and each of them had a different inaccuracy in the fence.
4) Get a smoothing plane, or possibly a plow plane.
5) Get a plow plane, or maybe a smoothing plane.
Smoothing planes are nice, and do some things a lot better than sandpaper. They're also fiddly to tune, and can be horribly frustrating. This is the first (and probably only) place I'm going to tell you to be really careful about what you buy. Look for a smooth sole, reasonably small mouth, and a lack of slop in the depth and lateral adjusters. Also, make sure you know how to sharpen. My favorite is a Stanley #3 that belonged to my grandfather, and I use it for most of the things people recommend a block plane for. That might just be because I don't have a good block plane, though.
A decent plow plane will change your life. All of a sudden, frame and panel doors are trivial, and you'll start looking for ways to work them into everything you make. That chair? Frame and panels for the back and seat! Building a box? Frame and panel for everything! The cheap one made my Mujingfang is sort of useable, or you can buy one of the millions of Stanley #45/55 planes or copies. Or you can find a grooving plane (the opposite of a tongue cutting plane, which is also really nice to have), and accept that your grooves will all be the same distance from the face of the wood. I'm moving in that direction, because mis-adjustable fences are starting to get on my nerves.
6) Finally, get a medium router plane from Veritas. It will do most of the things you want a router plane for, and it uses the same cutters as the large Veritas router plane. That'll save you some money when you inevitably buy the big one. (That should also go on the list, but it's getting longer than I want.)
In a machine-heavy shop, I'd start with a rabbet/rebate plane, then a plow plane. Then I'd go for a smoothing plane, to reduce the amount of sanding you have to do. Cutting rabbets (especially in small pieces) and cleaning up mortises or grooves can be a nuisance with machines, and is easy with hand tools. After the rabbet, plow, and smoothing plane, I'd go start looking for moulding planes, because they're fun, and you may never have a need for a jointing plane.