Hello AG!
I suppose you are talking about recreational flying. As said before, 2 things need considered:
1: Risk
2: Money
Point 1 has been discussed, flying is not suicidal or terribly dangeorus, and 40+ year old Planes are no problem. Learned to fly in something older than that myself.
For point 2 you already stated it would be OK for your situation and you would not impoverish your family (at least I understood it that way).
Besically, these questions arise a lot of times for things that are expensive (percieved as dangerous maybe) and are not objectively needed.
I once read a nice article by Bud Davisson, maybe this helps you along in making your decision:
Acrophobia - Grassroots
Best regards,
Purzel