You didn't answer my question.
I would certainly fund a 401K or Roth before prepaying a mortgage. But I can't ever see borrowing for a life insurance policy...
401 ks are tax heavy on the back end when you take the money out. In your program you'd pay off your home and take your 401k while your in a higher tax bracket because you have no mortgage deduction. For some people they pay more in 3-4 years taking the money in retirement than they deferred in 30 years of 401k investing.
RE provides more leverage for the long haul, which of course retirement investment is typically.
I don't know which of the questions I didn't answer. I don't sell insurance and we're well off, but not filthy rich? I just started this at age 50. Had I stared when I could have, say age 27, I might have much more money, but I used the tax deferred plan at work like all of the other lemmings and never shopped around or learned anything else.