It All Depends
Sure, if everything stays the same, there comes an age when you'll never get back what the life membership cost. But when is that age? It's important to use the right number for life expectancy, and that number depends on a lot of factors. The CDC and insurance companies have a lot of data online but you have to sift through it.
The usually-quoted-by-the-media numbers are life expectancy for babies born in a certain year, and includes all income levels, ethnic groups, genders, risk factors, etc.
But when you get more specific, the numbers look very different. For a white male who is 65 now, future life expectancy is almost 20 years, not less than 10. Nonsmokers can add a couple of years, smokers deduct a couple, etc.
Then there's the fact that things don't stay the same. 20 years ago, ARRL membership was $25/year, now it's $39/year. That's a little more than 2% increase per year. Depending on your income situation, that may be more money *to you* or less.
And there's more! If you renew for multiple years, (I usually do 3 years) there's a discount. If you're over 65, there's another discount on top of that.
Of course the big thing is the psychology of spending money. A lot of people will balk at paying one big bill for something, but will not question paying a lot of little ones.
73 de Jim, N2EY