How do you wipe out your paper money? Did he not keep enough to maintain his lifestyle stashed away in secure assets and went on a reckless spending spree?
There are tons of ways to lose BTC over time, scams like Trendon Shavers, Friedcat, Butterfly Labs; getting Zhou Tonged, Goxxed or Bitfinexed; more often than not, lost it in some ALT pump-and-dump or daytrading. But quite often, simply because people can't afford to hodl and had to sell to paid expenses/debt or emergencies. So it is actually quite difficult not to make wrong calls along the way that sees one's own BTC holding reduced substantially. Fortunately, due to exponential rise in fiat terms, people normally end up with more, in fiat terms, than years ago. But that still leaves a bitter taste for some as they know that they would have substantially more BTC had this and that not happened along the way.
Yep, there are a variety of scenarios that could cause bitterness, and let's say if you were in BTC for 3-4 years and you end up buying around 100 BTC and it cost you around $600 per BTC (average) (which would have been about a $60k investment), but then you make some pretty severe mistakes including some of the ones that you mentioned and even hackings or something, and you end up losing 80% of your built up stash.
At today's BTC prices you still have 20BTC x $19,000 = $380,000, and you are 6x in the profits, but you might still feel a bit bitter about the whole ordeal.
Overall, any of us can assess our current situation and continue to make plans that involve continuing to dollar cost average buy into bitcoin, unless we happen to be at the liquidation stage of our life - which, depending on health, might be someone in his/her 60s or 70s?.. and then in those circumstances, we might project how long we think that we have to live, and then schedule a draw down schedule based on such a projected timeline.. and sure the bigger of the two tragedies would be to draw to much and run out of money early rather than to have a considerable amount remaining upon death.
I think all of us who have been involved with BTC for a long period of time have some sort of regrets. We could certainly lose some sleep over the "Would have, should have, and could have" thoughts that race through our minds. Hey, even after hodling for several years and avoiding having our coins lost on Gox (got them off just a few weeks earlier) my husband and I still had some coins swiped a few weeks ago just trying to move them onto Coinbase to sell using Bitcoin QT. We double and triple checked the address we were sending them to as well (never had a single problem) but the address was totally changed behind the scenes somehow. We decided to do everything we could to protect what coins we have remaining. We purchased an entirely new computer and didn't even connect it to our network and used our backup disk to load the coins onto it and bought a Trezor. I guess there is a feature on the Trezor where we can check the address being sent to on the Trezor itself for security. That is necessary we now can see. We had several people ask why we didn't send a very small amount of coin first. Well, since we never had any problems and this computer that my husband uses is checked repeatedly for viruses and I don't even allow myself on it (I don't trust myself to go to sites that might access a virus of some sort) we just trusted it was fine as it always had been. But the hacks are becoming more sophisticated.