Please help w/my communication model

Hello,
I am launching a website about a Sports Investing System in the next 2 weeks. We will be providing a system for sports bettors to follow. The revenue model will be a one-time fee for the whole year or a monthly subscription model. A lot of consideration has gone into the variables incorporated into the picks and the system has been successful over the last few years. We have a list of 150 people we send out the picks to everyday (or when appropriate). Everyone loves the system so we decided to launch a site... Anyhow, my question is about the communication model for non-paying members. Let's say, someone comes to the site and converts to a non-paying member. The fill out our form, we issue a 60 day free trial. Hopefully they will love the system and want to become a paying member. We will be using Infusionsoft. Below, is what I am thinking for a communication model to create conversions from non-paying to paid subscribers. Any opinions and advice for improving the model would be greatly appreciated. Thank you in advance for your help.

Day 1 - They receive an email titled instructions for SIS. We also explain the system is $57.00 a month after the 60 day trial period but if they sign up now and pre-pay for the whole year they will only pay $288.00 and save $360 (offer expires in 24 hours) This breaks down to $24.00 a month

Day 2 through 60 - They continue receiving the picks everyday for free

Day 7 - Promotional email, sign up now, pre-pay for the whole year and pay a one-time membership fee of $324.00. Making the monthly fee only $29.00, saving them $336.00 a year! Offer expires in 48 hours

Day 31 - Promotional email, sign up now, Pre-pay for the whole year and pay a one-time membership fee of $408.00. Making the monthly fee only $34.00, saving them $276.00 a year! Offer is valid until the 60 day trial expires

Day 45 - They receive a reminder email about the offer letting them know there is only 15 days left to act!

Day 58 - They receive a reminder email about the offer letting them know there is only 2 days left to act!

Day 60 - They are notified their membership has expired. General results of last 60 days are recapped. They are reminded they can join for a monthly fee of $57.00

Day 61 and on - They are moved to a different group in Infusionsoft. We send them a dally email with results but no picks, affiliate links to our recommended sports books and a link to register and become a paying customer until they opt out or become a paying member

Thank you!