I used to get to the airport last minute, mainly because I noticed that I was spending too much time just waiting. That has changed over the years. I don't get there 4 hours ahead of the flight, but it's no longer 45 minutes either. I agree with you on that one.
Also good point about the shuttle to the airport. I surprised me how many people dismiss things simply because they're supposed to be more expensive. I've stayed at the Rennaisance in Vienna for less than the cost of a 3 star hotel in that period, for no other reason than just because I checked. It helps to be open minded and check what you think might be more expensive; it may turn out to be quite the opposite.
I don't really ask for UGs when it comes to cars or hotel rooms. I've gotten plenty, but never because I asked. As a rule of thumb, it always helps to be nice to people who provide a service, be it a hotel check-in person or wait staff in a restaurant. You catch more flies with honey and you can see it all too often how demanding people get the short end of the stick.