If I only picked what grabbed my attention, as I was doing initially, I'd have wound up with a bunch of fougeres and ambery fougeres. Fortunately, Grant used to have a neat little fragrance suggestor about 11 years ago, which categorised a small number of scents into different groupings. I really disliked some of them at the time, and was ho hum about many others, but wound up buying most of them as they went on sale. I forced myself to wear them and grew to like lots of other categories.
Nowadays, I just buy heavily discounted scents. The only criterion they have to have, is that they have some presence rather than being lame. I usually wind up getting quite interested in them, even if I didn't like them much initially. At the end of the day, a perfumer spent quite a bit of time composing them, and it's interesting to see if you can eventually see the same thing that he or she did when composing them.
If you haven't already done so, download the Leffingwell/H&R Masculine Chart. It's getting old now as the last entries were made in 2000, but many of the scents are still on sale. It'll give you an idea of the range of scents, and of which categories you may be ignoring - but ultimately missing out on.