I was 10 when Tron came out. With me being into video games and computers at that age, Tron made a huge impact on my childhood.
That being said, the film hasn't aged all that well. Some of the dialog is cringe-worthy. I still enjoy it, but at a sentimental level.
Tron Legacy, however, was a much deeper film, that explored more ideas than just being trapped inside a computer. It's really Flynn's story of watching his creation run amok because of his own shortsightedness, and not realizing he had everything he needed (Sam) right in front of him the whole time. That's an ageless story, not one stuck in early 80's computer jargon (Bring in the logic probe! No, null unit!)
Do I think Tron Legacy is perfect? No. It's stupid that Sam had his street clothes on when he got zapped inside the system, and that the Sirens had to give him that outfit. As shown by the original movie, the costume is part of you being a program. They are inseparable. Also, don't get me started on Sam bleeding.....