The very best thing you can do is get one kit that will do everything you want/need a kit to do, and take care of it so that it can take care of you for years to come. This is likely to take some research and patience, but you'll be thanking yourself later.
In 1998, I decided to upgrade from my Taiwanese stencil kit to a decent lower-end kit. Modern Drummer had just done a shootout between several different drumsets in the price range and this influenced my decision greatly. In the end the Tama Rockstar and the Yamaha Stage Custom were the big winners. Fortunately, my local shop carried both those brands and I could side-by-side them. I walked out of there with a six-piece Stage Custom and later bought another floor tom for it. This meant I could indulge my inner prog cravings at home and take a four-piece to that straight-ahead blues gig too. The hardware was, and is, some of the best in the industry. The kit sounds great, too; I constantly get comments about its sound at gigs. I've played that kit for pay and for fun ever since. The only reason I have a second kit now is that someone gifted me a vintage Ludwig kit in poor shape and it was nearly as much fun restoring it as it is to play it.
It's obviously much easier to do this sort of comparison shopping for lower-end kits, which can be found anywhere, than it can be for high-end kits. You pretty much have to know somebody who owns one, or be conveniently close to a good drum shop, to test-drive a top-of-the-line kit. But if you want to make a good investment (and that's what it is, an investment), it should be worth your while.
I don't recommend that folks trying to figure out what they want in a kit buy a custom build or an exotic material kit like eucalptyus/bamboo or acrylic. You want the kit to be a jack-of-all-trades unless you already have a specialized need or know exactly what you will be using it for. If you play drums in a Zeppelin tribute band, you have a pretty specific shopping list. If you play drums in a blues band, a Dixieland jazz band, a top-40 covers band, and a theater pit band, you may want a more average-sized kit such as a 10/12/16/22. Maple and birch are safe go-to shell materials.
This will sound like heresy, but people spend all this time trying to buy great-sounding toms, tune them to sound awesome like on the records, but the kick drum which is played ten times as much is overlooked. Buy the best-sounding kick on the block, and the best-sounding snare, and some great cymbals. You play the toms maybe once every sixteen bars on average, and for that short amount of time you can easily get them to sound more than good enough. A weak, non-projecting kick can cripple a groove.
My main kit is a shell bank with every even size from 8" to 20" (except an 18"). this allows me to set up a huge kit for that crazy metal or progressive project, strip down small and lean for that short acoustic set, or even do something silly like use the 8", 10", and 12" as toms and the 16" as a kick on a lark.
It's not weird at all to have one kit for a long time, just so long as you buy a good kit that works for a wide range of situations that you can take care of.