I've been in a wheelchair full-time for the last 8 years or so. (I used the chair before that, when I had to walk long distances...longer than a couple of car lengths). Asking for help at first is hard, as you identified...but for the most part, people are gracious and happy to help.
I still travel by car alone...and call in (like to a hotel) to tell them "I'm here in your handicap lot; I'm registered to check in to your hotel; can you send someone out to help with my chair?" I've never been refused, the hotel workers have been more than helpful, and I've never felt uncomfortable doing it. My going off on my trips (I do some consulting work) is good for my husband, too, because he gets a break from having to worry about me at home (instead he worries from afar; thank heavens for cell phones! :) )
Happy holidays to you and your family, too.
...I am not a doctor, nor health professional, and don't pretend to be one, here.....