Help with Macro - sending an email based on cell expiring

Hey all, I am new around here and not sure where to begin or how to start into macros. I have a complicated (in my mind) issue I would like to automate and was hoping I could have some assistance?

The goal:
Send one email to each supervisor to include any of their employees who have training that is within 60 days of expiring, or is already expired. For example, "supervisor 2" has 3 employees, is it possible that when the macro is run, that it will look at the dates, determine which ones are coming to expiry, then send an email with the persons name, the courses that are expiring and when they are expiring in a list or chart in the email?

I have attached an example of the type of spreadsheet I am using for reference. Row 1 is the headings, Column A is names, B supervisor, C supervisor email, then the rest is the training info.

For example, is it possible to have it return similar to this:

Supervisor 1,

The following employees have expired training:

Jackson, John - Confined Space, OSSA FALL PROTECTION, Ground Disturbance Level II, H2S Alive

The following employees are within 60 days of expiring for the following training:

Jackson, John - Elevated Work Platform (EWP)
Monument, Mike - OSSA FALL PROTECTION, Elevated Work Plaform (EWP), First Aid

Please respond to this email if retraining is required.

Sorry if this is a burden, even if someone could provide me with a good source to figure it out on my own that would help, I am a newb when it comes to Macros.

Thanks in advance.
Andrew