I am sure in the future I will move to segwit, address that start with 3s, then to native segwit (bc1q) a few years later, and so on. This is the strategy that I deploy.
Strange scheme for me. Why not to move to bc1q addresses at once and escape the nested segwit stage? You would save some of your stash by doing so. This would be natural for the penny-savers, unless they wanna the extra payments to miners to appraise their job . Any plot from your part here?
Among all others mentioned in this thread advantages the native sigwit addresses (opposite to legacy ones ) use the small character set which eliminates error at transferring them viva voice.
As I tried to imply in my comment, I am not concerned with saving pennies. I am more concerned with security. I will move from one protocol to the next in the order that they have been around from oldest to newest. That is my strategy.