every one I talk to tells me to go for what you want to do WHENEVER you want to do it and to not be afraid of change. I grew up in a household where my father ran his own bridgebuilding business. As the scale of highway projects grew, larger businesses took the lions share of the projects as the companies that had the cheapest financing over all the capitalized equipment/cranes won most of the contracts. I tell this story because my father was a successful small businessman for 25 years, yet when the writing was on the wall that small companies weren't going to last, he was afraid to correctly react to it's implications...and sadly went bankrupt after turning down several buyout offers. This happened to him because he could not face trying to do something else. He chose to try to ride it out...wrongly.
I'm in more or less the same boat as your dad was and I decided to jump ship before it took me down with it. Also, I am coming from a career field completely unrelated to science.
As for age, I think it is in our favor. Every dentist or administrator that I have ever spoken with has also felt this way.
I was just accepted to the dental school of my choice and I firmly believe my age was a huge asset to me in accomplishing this. I'm 33, married, and have 2 kids (12 and 1 yr.). I returned to school full time to complete 2 years of prereqs with a 4.0 science GPA all the while continuing to work 30+ hrs/week (a reduction from 80 hrs/week) and raise my family. Interviewers are looking for motivation, maturity, and commitment. Nothing shows these qualities more than an adult who can uproot his/her life when it is least convenient, redirect, and successfully balance work, family, and school. My interview went very well and seemed more like a casual conversation among adults. Additionally, years of life experience gave me a lot to draw from when answering questions.
As a side note, school seems much easier the second time around. This is probably because the first time I didn't have the rigors of balancing work and family to compare it to. I'm forced to be efficient with my time now.
As for the alternative student life being somewhat lonely, I was very fortunate in that I met a group of students that were all close to my age, married, had kids, and were pursuing medical fields. We instantly formed a study/support group and it was this comradery and pushing each other to succeed that got us through and into the schools of our choice. I hope to find such a group of friends again in dental school.
BTW, I was specifically asked in my interview how I felt about graduating from D-school at the age of 38. I replied, "I'm going to be 38 regardless whether I'm a dentist or not. I'd prefer to be a dentist." which got a chuckle from them. I told them that I still would be able to devote nearly 30 years to the field which they agreed with.
For those of you even older, I say go for it. I know a dentist who was accepted into dental school as a 40 year old single mom. She lived through it, graduated 10 years ago and bought right into a booming practice. She loves every second of it and is doing very, very well.