Skateboard Maintenance
One thing you can count on in skateboarding is that eventually every single piece of your gear will break down. You'll get holes in your shoes, you'll get flatspots on your wheels, you'll get dirt in your bearings, you'll grind down your trucks, and your board will snap. It's something you've got to deal with, but there are some tricks you can use to slow down the process.
First up; Shoes. Shoes can be the single most expensive piece of your setup, and unfortunately they're also usually the first to end up in pieces. My first piece of advice would be to stay away from suede shoes if you can. I know there are some good lookin' suede shoes with great boardfeel (eS accels, reynold 3's), but don't expect them to last more than a couple weeks. Leather is a much better choice and will last you about twice as long. When your shoes do start to fall apart, though, there's one way to prolong the magic: Shoe Goo. Shoe Goo is god's gift to skaters. This stuff costs less than a happy meal and will keep your shoes going long after they should've been dead. The best way to use Shoe Goo is to smear some on as soon as you see the fabric start to wear down--don't wait until you've got holes in your shoes to fix them. Put a fairly thin layer down, wait about 10 seconds for it to harden a bit, and then flatten it out with your fingers. Let it finish drying overnight, and reapply when you've worn down to the fabric again. You just saved 50-80$--that's over 100 tacos.
Another way to keep your gear going is to love your bearings. There are a couple ways to do that. First off, take care when you jam new bearings in to your wheels. Most people put their bearings on a truck axle and push the wheel on over them. That works, but there's one problem you'll run in to here. The more you have to jerk the wheel around to squeeze that bearing in to the hole, the more likely you're going to gouge the inner tracks and ruin the bearing before you've even set foot on your board. Push down as straight and hard as you can and you can minimize that.
Another good habit to get in to is to clean your bearings. You can give 'em a quick checkup without even popping them out of the wheel. Some people take them out, put them through a bearing washer, remove the shield, add a drop of lube, and then put them back together. If you've got the time and patience, that's a good idea, but you risk damaging the bearing when you yank it out of the wheel. I'd recommend a different plan. All you need is some Speed Cream, a tissue or rag, and a wrench to get your wheels off. I don't recommend water or WD40--water can rust your bearings if you don't get them 100% dry afterwards, and WD40 can leave a sticky film that attracts even more dirt.
Alright, take your wheels off and put a drop or two in a bearing depending on how dirty it looks. Take your tissue or rag and give the bearing a decent wipedown. Once it's looking clean, put another drop of Speed Cream in the gap between the outer ring and the shield. Hold the wheel by the inner ring (don't touch the bearing too much) and give it a good spin while turning the wheel right to left. This helps work the lube a little deeper inside of the bearing. Do the same for the rest of your bearings and you've got a decent quick tune-up.
One last piece of advice for protecting your bearings is to get a set of rim guards. Rim guards replace the nut on your truck axle and can keep dirt and water from splashing up in to your bearings. They're built with a shield on each nut that covers up your bearing inside of the wheel. Rim guards are only a couple bucks, and they can go a long way toward protecting your expensive bearings.
If you keep all of these tricks in mind, they can really go a long way towards saving your gear. Most people (Yeah--me too) learn the hard way, and skateboarding ends up taking a big chunk out of their wallets. After awhile, though, this stuff will be second nature and you'll probably come up with a couple good tricks of your own. Pass it on to your buddies and if you do come up with another good idea, shoot me an e-mail.