Like kim said...entitled=NO, but it never hurts to ask. Often in situations like yours the key is the correct approach and with the right person.

Traveling in January might be even tougher for an upgrade as it is high season and many places are full or almost full. Asking ahead of time (on a space available case) would be a good idea also.

Loyalty does not seem to be viewed like it once was and that goes for everywhere. Unless the business is actually tracking your loyalty and has a stated loyalty rewards program, I would not expect anything in today's world.

In 25 years (1991-2016) I have made over 40 visits (that would really throw the math off!!). Other than sometimes being recognized by people I have dealt with in the past, it is business as usual.