I don't think flying is a hassle. Leave yourself plenty of time, prepare for waits - bring a book or something to listen to. Inform yourself thoroughly about security procedures and baggage allowances.
Where possible, fly from a smaller airport. Less people, shorter distances, less chance of luggage getting lost.
As others have said, choose your seats carefully, choose a flight that is at a suitable time of day. Include an overnight stay on the way if necessary.
Check in as much luggage as possible. It's the walks across the airport with a heavy handbag or backpack AND a small suitcase which make it so stressful.
I love browsing the shops at the airport because I live in the sticks and don't see many shops.
Above all, consider the flight and the time at the airport (don't let delays get you down) as part of the holiday. Once you shut the front door behind you, you are on holiday and have the right to enjoy everything that happens.
Just leave yourself loads of time and listen out for announcements; be prepared but be relaxed.
Prepare yourself for your destination. Once you start reading up about a place you will find more and more fascinating details about things and will start to look forward to being there and seeing it all for real.