You can try a mix of Wordpress + Gravity Forms + Cart66 (these two integrate) for selling subscriptions which require detailed information submitted by the customer. Thats the easiest out of box solution I've found for this type of stuff.
I vote for Wordpress + Gravity Forms + Cart66. I've used that for many different scenarios including services and even educational classes. Great way to get custom data and process orders all at the same time.
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