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Grow a set of balls and make a decision.
If the towns high school is mediocre in hockey in CT: is there any age you pull him out of club hockey? or just go club mite to midget?
And if he has an honest chance at college send him to prep.
Be realistic, which mostly likely means you should get off the road to nowhere and encourage him to play high school hockey. Youth hockey pretty much ends after bantam minor. If he has a great first couple of years of high school hockey he'll get offers to move on and/or he and you will have a better idea of which direction to go.
I know in mass if your a good player with decent size it is better to play on a d1 hs as a freshman vs staying back, to be on a future prep team along with FS bantams. If your really good prep teams will reach out sophomore/Jr year if you want to go that rout.
Yes every year is different, per Catholics d1 it may be hard. in strong town HS it depends on what they need, how good, size, competition at position. Some years easier, some not. My son will be a freshman next year but is a U15 (late birth month). So we will play half season U16 and see if he makes the HS team, not many options for full season U15/U16
Just look at the CT All State teams. Most of these kids are jv prep players at best. Frankly, a few of them would not make jv.