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If someone isn't sure, I think going in enlisted first is a good option. It gives you valuable and practical experience which can be relied on later no matter which path you choose. On a team, I find myself relying heavily on my Infantry background and I can only imagine how much more knowledgable I would be with enlisted experience.
The only downside to going enlisted first, then wanting to remain in the SF Community as a CPT is the 3-4 years you have to spend in CF as a PL before you can go back to the Q. But then again, that is also a valuable perspective for a SF Officer which has to maintain good relations with the CF battle space "owners". IMHO, you have to take a more "zen" approach to this path and find value in the journey and not just the payoff of reaching your long term destination.
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