Step1
First and foremost, I see that kids will fight to work for money so they can afford the skategear they need. My impression (based on my other two) is that there is no more passionate a money-maker, than a passionate skater. Give them tasks, and they will perform. Anything to get that deck or those bearings or those new wheels. Not to mention the $80 shoes and $60 skinny jeans!
So, first, get these stores in your head or in your favorites. Ross. Ross is irregular clothing, but the most important thing is that they often have the brand. It doesn't matter if one sleeve is longer than the other as long as the shirt says "Volcom" or something similar. In addition, Ross carries Vans. Now in our group, Vans are not apparently the most popular shoes, but my son will take them if the alternative is army boots. At Ross, they run less than $20. In addition, we found Volcom skinny jeans and a green striped must-have sweater. This was apparently a $70 sweater, but being irregular, and at Ross, the one we bought was $12. (Caution though, check labels. Family members will wash this 100% wool sweater and shrink it to doll size. At least you'll be glad you didn't spring for the $70 version).
Last, but certainly not least, DO NOT wait until the shoes are needed. eBay has continuos listings for $80 shoes. You will not always (or even often) win bids for $15, but if you bid every time, you will win now and then. Know your kid's taste so you know what to get. A bargain is not a bargain if they'll never wear it.
eBay is also a necessity for skate decks. They are sold in lots by a handful of reliable sources. There is no skateboard out there that is unbreakable, and you may as well get the most bang for the buck (be sure you get the decks with grip tape on them already unless you want to get stuck with the application of it). Buy the lot of 5 or 10, and it will be much easier for you to cheer your young Tony hawk on while boards break.
Step2
The next step is about the lesson. My son has gotten much better at bargain shopping and hanging onto his stuff now that he is earning money to pay for it. This is a great lesson in money management. he used to trade clothes, but now he knows the value, and it doesn't happen anymore. He will do anything extra around the house and earn $5 here and there, because he has his eye on a new deck.
Lessons learned include - take care of the stuff, shop for bargains. Make the skateboarding itself more important than the brand name on a new $120 deck. He also knows how to apply grip tape, change out bearings and hardware, recycle/reuse wheels, hunt down spare hardware in the garage, etc.
Step3
Shoe Goo is a must. This stuff has apparently been around for a long time, but I had never heard of it until I - in my frustration - began searching for solutions to the three month disposal of expensive skate shoes. Now we save money on the great shoes, AND every time he comes in from tricks, we apply shoe goo to the affected area. The new shoes ($80 ones I got for $15 for Christmas on eBay) have one scratch that has been covered by shoe goo, and no holes! It is a miracle. The right foot always gets a big hole right in the smaller toes area. I often think these shoe makers would make a killing off selling single shoes instead of pairs.
Step4
Now that you have hints and direction for making this a less expensive venture, the last step is to reinforce this sport in your kids. We've all seen the 'no skateboards' signs, but things they are a changin'! Last week I signed a release for my son, because the High School finally decided if they can't beat 'em, to join 'em. With some work between the Staff and Legal, they came up with a way to allow skateboarding as long as the kids wear a helmet and sign the release form.
Way to go Hutto ISD! My son hangs out with about 15 solid good kids who love skating as much as he does. Allowing them to skate has removed the need to replace that with something unhealthy. Parental positive reinforcement and guys like Tony Hawk (because these kids ARE good and daring) has also helped them feel better about the skateboarder stigma that was around for so long.
Not to mention - do you have any clue how much money professional skaters make?