I've never met either, but I see the milkman's daughter every morning. If I ever find that guy... j/k lol
In all seriousness, I've never considered tipping either. The mailman doesn't even come to my house. He goes to a community mailbox unit a block from my house, where all 80 homeowners are required to pick up mail.
The trashman stays in his truck as he picks up the trash can with a big hydralic arm. I've never seen or spoken to him, since he comes while I am at work, as does the mailman.
I don't receive the newspaper, but if I did, I would probably tip him, since I know that job sucks (my dad used to run a route when I was a kid). My brother and I also used to deliver a weekly paper called "Grit" along with the TV Guide when we were kids.
My mom and dad used to also get milk delivered to our house. We had an insulated box on the porch and the milkman would place glass bottles of milk in it so they would stay cold. The last place I saw milk delivered was in Colorado Spings in the early 1990's.
Tipping these delivery people is a nice gesture, and I am sure it is appreciated, but unexpected. Most people now never meet the people that add convenience to their lives, because both parents normally work these days.
This thread brought back a lot of good memories of simpler times.