First, buy some cheap crap

There's a classic style of post about just about any kind of photographic equipment that shows how starting with cheap equipment and gradually going to better and better gear is much more expensive than getting the better gear to begin with. These posts always irk me, especially when accompanied by exhortations to get the finest, most expensive gear that's out of the range of most mortals.

My approach has been exactly the opposite: When going into a new area when I don't know what to look for, I get something cheap that I expect to get rid of in a year or two. Whether tripods or flashes or
studio lights, I look for a third-party or store-brand kit as a "learner set". I'll then use that plus various internet sites to learn how to use that thing and what it is I like and don't like about it. I have found this to work a lot better than trying to understand what's useful and what's a gimmick based on internet reviews.

Once you've figured out the basics of this new type of equipment, it's time to get a reasonable one. This is where the mass-market brand-name items come into play. You can now reasonably look at reviews and comparisons, disregarding things you've found are unimportant for you, and up-rating what's really your thing. I bought my 60D this way: I made a spreadsheet of the features I wanted and the cameras that gave them. Since some features, like a flip-out display, are relatively rare, it cut down the selection to where I could borrow or rent the options until I knew what to get. I didn't do it when getting a tripod, but was lucky enough to be able to sell the Manfrotto that didn't suit me for a small loss.

The medium-quality item is likely to last you for several years, during which you'll figure out if it was just a short infatuation with a particular method or technology or something you want to specialize in. If the latter, you will surely learn enough by then to get what you need, rather than what people are trying to push.

If you tried getting the very best quality from the beginning, you're as likely as not to get something that's not suited to your needs: Too big, too heavy, too specialized. And even if you get a thing that suits you, you might find that it was just a passing fancy that you spent thousands of euros on instead of hundreds.

The main point is to make a conscious decision to get a "learner set". Know that it will be sub-par and adjust your expectations accordingly. Then you'll have a better chance at getting what you really need later.

A final note: Don't apply this to items where your safety is at stake.

My equipment

For those into the technical details of my photography, here is my current equipment:

Canon EOS 60D - just upgraded this month, after rigorous testing of the alternatives. I knew I wanted a flip-out screen, and that fortunately limited my options. The 60D won out by having much superior controls, which by now is the more distinguishing factor.

Canon EOS 350D - my first DSLR. It's old and has crufty AF, so it plays backup camera.
Canon EF-S 60mm f/2.8 Macro - my most beloved lens, it renders beautifully but is not long enough for photo walks. I use this for portraits as well as macros.
Canon EF-S 55-250 f/3.5-5.6 IS - my walk-about lens. Long enough to capture details, barely wide enough to get context shots.
Sigma 18-125 f/3.5-5.6 - my "vacation lens". I end up regretting whenever I only bring this, but I have nothing else that's this wide. It renders flatly and with smushed colors.
Canon EF 50mm f/1.8 - for low light.
Induro AX-214 tripod - very flexible, good sturdy design, comes with a nice carrying bag and a little bag with extra spiked feet. It's nice.
White foldable bounce, 60cm wide - portable yet useful.
Strobist flash - somewhat less automatic than Canon or even Promaster, but very flexible powerful for the price.
Canon remove release - best $25 I ever spent on camera equipment. Lives unobtrusively on my strap and allows immediate or 2-second delay shots. Nothing else, and that's what I need.
Lightroom 4 - my favorite photo program. It slices, it dices, it even uploads to this blog.
CarrySpeed shoulder strap - solves the problem of the strap having to slide around your shoulder when bringing up the camera. Well worth the €50.

I have a penchant for the odd combinations (as evidenced here and here), and they're fun to play around with, but I will eventually need something better than what I have now. An ultra-wide, a better mid-range, perhaps, and a body with good AF, swivel screen, better ISO and per-lens micoradjustment are all pretty high on my list.