Well, most of those have moved out of Pittsburgh, the closest is Greensburg. I am also planning on buying the right size as needed vs. the room to grow approach. I actually just auto deduct $10/month into a savings bucket for his skates. With that plus selling his used skate each iteration won't be too bad money-wise. Plus I have so much lightly used hand-me-down elbows, shins, pants, etc. I don't have to pay for much other than skates for the next 2-3 years so that is a nice luxury. The used skate route is good but honestly I don't know that I have the time to track down the appropriate skates.
It's just difficult to buy the right skates for someone other than yourself, especially a kid who doesn't really know how to describe what it going on inside the skate, may confuse the fact that the skate is stiff for not fitting, etc.