For younger kids - under 16/17 definitley spend the money on instruction first. Even then it boils down to disposable income - if you have 10K of income to spend on your kid, and won't miss it - what the heck.

No disrespect, but Tecumseh would struggle with most PBLO teams, ECPL as well, although probably close to .500 with them. In a one game series anything can happen though.
The Windsor area is unique (and talented)- and no doubt when you look at pure value - miles ahead of most other areas. geography factors in a bit, and an early start - late finish always help.