We could hold this same conversation with houses, cars, airplanes, etc... what it boils down to is somewhat 'envy' factor? Who knows... we all play the Joneses to some point in our lives... my boat is bigger, faster, newer, etc.
Yep, that's it; Rolex envy! If you own a $2500.00+ watch that doesn't keep as good time as a $30.00 piece of cheap tech, but you can't wear it if you are sailing (watches do get torn off and the expensive ones do NOT fall on deck), wandering ashore in some 3rd world country, or some places in the US (only a fool would make himself a target), or working in the engine room, then it is, just as you said; an investment, not a time piece.
I wear a watch to know what time it is. Gosh, it's a real purdy one, too, but it's only about 40 bucks and no big deal if I lose it.
Our phone has 3 sim cards (out of 12 island countries), mainly for outgoing calls, so it's most often at the chart table, uncharged, so that won't work for us.
There are two sides of the coin here; those who wear a watch and sail occasionally, and those who wear a watch and are on their boat almost every single day of the year. Few in the second group would wear a Rolex, even if it were given to them, I believe. We've paid our dues to get where we are, and if any of us had felt a Rolex was a priority, we could have bought one along the way. Envy, I think not.