At what point do you all email respective customer service to get points if your flight is delayed? 1 hour? 2? Also, do you be blunt and ask for it or circle around the topic?

Blunt 1 hour. Ask for number of points you want. Sometimes it's less but always round up

I always just describe how the problems could've been avoided if they do their job correctly and show that I am disappointed in a polite manner... Have a total of at least 40k miles from like 6 emails with the max one being 15k, so I guess my approach works ?

@d1 what is an average number of miles to request for say, an Atlanta to New York flight and a 1 hour delay? Does this work for most airlines? My mind is blown right now

@pwc1 can you post the email :-)

Let's be clear - you need to have some legit status on the airline before they start just giving away miles for your 1hr delay

5 minutes - they will give you points!

TPG advises to phrase it as asking the airline for "a gesture of goodwill" for the delay/issue/etc.

Status will matter, I got 4K for like a 1-2 hours delay when I was silver while my senior who used my email template got 5k... But free miles is free miles!