I've gotta say, the whole tipping thing is very awkward for outsiders.
I mean - you go into a hotel, and the person who shows you to your room is massively friendly to you... then you realise it's only because he wants your money. It just feels very false, and you come to resent it very quickly. The only other places where the whole tipping thing is so big are third world countries.
I'm cool with tipping waiters, because I think it's a good plan to make nice with anyone who serves you food, but everyone else? Get a better job if you don't like it. Damn straight I've never worked in the service industry, because I had the sense to find better ways to make money without slaving my ass off.
I remember when I took a vacation to Dominican Republic and I signed up with one of those travel agencies where they hook you up with transportation from the airport, and so on. Well the people that greeted me at the airport took my bags (2 bags), and they brought it over to the bus. When I got to the bus, I handed the man who carried my bags $2 for the 1 minute walk to the bus with my bags. This guy literally pushed my hand back and said that he expects $10 tip for doing that. I was so taken back, $10 for fucking carrying my bags for about a minute? I could have done that job myself, I didn't even ask him to carry my shit. Anyhow, he ended up taking $2 and I got onto the bus.
Then I had to tip the bus driver.
Then I had to tip the people at the hotel that carried my bags upstairs.
Then I had to tip the maid to clean my room.
Then I had to tip the bartenders even though all drinks were inclusive with the stay.
Then I had to tip the waiters at the restaurants even though all food was inclusive.
Then I had to tip the tour guides for the places we visited awhile that was also inclusive.
That was quite a vacation.
But staying back on topic, I don't mind tipping. I do think it's shitty that restaurants save money on salaries by increasing the expense for the customer. I feel that all restaurants should pay at least minimum wage to the waiters and the 'respected' tip % should be 5% at that point. I do feel stupid sometimes when I have to tip $30 for a 3 person dinner. Though as long as waiters are getting paid below minimum wage, I feel it's the right thing to do to markup the order by 15% and more. Luckily I've never had horrible service, so I haven't had the need to leave no or little tip. I also tend to eat at the same 4/5 places, so to save face I need to go along with the norms.
When it comes to delivery man, I don't mind tipping at all. Being able to get the food straight to my house without dressing up and driving is great. Considering that usually any food that I get delivered only ranges in the $15-$35 price range, I leave about $5-$8. Enough to cover the gas for the delivery, and some on top.