I assure you, Uberman regrets having children. He has not come to terms with it just yet, at least publicly on here.
I've been thinking the same. He took a big risk (of spending his whole life semi-miserable for a goal that may be achieved or... not), now it's very important to convince HIMSELF that it was worth it. That's an inner battle of one person. Just being faithful for one female for decades (for an attractive male. From what I remember he's good looking. no homo) may be a curse. And that's just the obvious, many many other stuff.
We all have our own inner battles in this ridiculous experience called life. Nothing matter at the end, just while we are still alive.