Save $30 and spends hours of your, obviously worthless time (according to your boss), and use your own SSL cert. Don't argue with the boss. He obviously knows more than the experts here do. Then we things get to be a royal PITA, buy your $30 certificate.
I will not waste my time arguing over trying to save you $30. Either do what we recommend or what your boss says. He is in charge of your pay so I know who I would follow. Just document our conversations here to CYA when things don't go well.
I will be gone all week so I will not be back on EE for another week.