While I agree that your pricing makes more sense to the customer, consider that $99 is only 17 months.

Someone who signs up with this service and sort of forgets about it or thinks about it like life insurance (just another small monthly bill), could be a paying customer for 20 years and ultimately be worth $1,200 to the company.

Couple that with the monthly fee model is much easier to pari with a "3 months free" offer, and the current pricing may be optimal for the company even if it results in significantly less signups or a less common sense pricing strategy.