I am a parent with mental health issues. My boys are 23 and 29.

I tried to over compensate because of guilt I have for not raising them 'right'. But I think about it a lot, it might be because I was insecure and felt guilty for not being someone else, and wondered if I had the right to be alive.

In spoiling my children, and trying to give them anything they could desire, really what I was doing was saying, "I am not good enough for you, all I have is what I can offer".

Perhaps he is trying to over compensate too. It isn't your responsibility to help him develop his own life, but perhaps you can say, "I have everything I need, you did well. What I do need, is for you to be happy with how you did, and not live in the past, or wonder if you did enough. Thank you, but your job is done".

Not that exactly, but I think that is the message we parents who feel we can never do enough need. At least, it is what I needed.

I am glad you love your Dad, and want him to be happy.

It is incredibly hard to learn how/when to STOP parenting.

Best of luck to you.