Formula/Macro to determine when 90 days have passed from pre-defined date

I have a requirement in which I need to send a customer a disclosure form for 2 scenarios: (1) send a disclosure form for an initial purchase and (2) every time the customer makes an additional purchase, I need to send another disclosure form if 90 days or more have lapsed since the last disclosure was sent.

For example, assume the customer makes purchases on the following dates:
January 1
February 15
March 1
May 1

I need to mail a disclosure on January 1 (this is the initial purchase)
I need to mail another disclosure on May 1 (120 days have passed since the January 1 mailing)
The disclosures for Feb 15 and Mar 1 are suppressed (only 45 days have passed for the Feb 15 date; only 59 days have passed for the Mar 1 date).

Once I have mailed a disclosure, the "clock" starts over. Continuing the above example; if the client makes another purchase on June 1, the disclosure is suppressed (only 31 days have passed from May 1 to June 1).

I have attached an example with sample data and expected results. Any assistance appreciated. Thanks