get a throwaway email address at like hushmail.com or something? for someone who's so into privacy, I don't think you've made the effort to figure out some solutions to privacy problems.
makes sense that this should work if ran on a flaskapp, never tested it tho to be honest,
in the past hour tho I moved to hushmail.com smtp service and it works just fine :P with 0 lines of code changed and only some config values modified on the server so it was actually very easy to change to that :D
next time I need an smtp service tho I'll give good ol' smtplib a chance and use gmail with it to see if it works. it's also worth mentioning I didn't use port 465 but 587, maybe that causes the issue on the gmail end ¯\_(ツ)_/¯
In my case I began ordering from bud buddy in 2002 or 2003. There was an order form you printed from their website and indicated your first and second choice of strains. They also offered chocolate chip cookies and pre-rolled joints IIRC. I think it was budbuddy.biz... Anyway you printed off the order form, put your return address on it and your hushmail.com email address and mailed it in with cash or a money order. BB was posting on the Cannabis Culture magazine forums and that's where I found out about it. The weed was always compressed and deformed but holy shit did getting west coast quality weed in eastern Canada ever make you popular!!!
Then Budmail opened up.