Strictly in the "FWIW" dept, over the last 20 years we have had quite a few club members repaint their topsides and decks on older (i.e. pre-1980's) sailboats. I know of two members doing a roll-n-tip, at least one other that had a local yard use a one-pack epoxy paint, and the others were all hauled out for professional spray work. Some of the pro jobs were poor and after 8 or 9 years are not holding up well --- one was done by a truck painter and reportedly cost half what a yard would charge but was worth less than that, IMHO.
At least 5 boats currently in the moorage were painted by a pro painter/ship wright in his enclosed shop, and his work typically looks "like new" for over 20 years. Not inexpensive, but his normal process is multiple color coats and then multiple clear coats. Only a
few new boats have gel coat that look that good. And ten or twenty years later that shine endures.
It is OTHO going to always be about three things: 1) Protecting the underlying FRP from UV detonation once the original surface layer of gel coat is too thin/gone, and 2) restoring the original appearance/shine after decades of repairs and divots.
And of course, for #3) there is the question of
Money.... if keeping the boat for over ten or twenty years, major restoration Will amortize out in use and pleasure.
Purely Subjective... yup, 'tis true.
And, when selling, a great looking boat will sell much much faster than the other 95% of similar-age craft. Given that "time is money" this can be significant in a crowded market of used boats. I have watched owners spend over a year agonizing over the lack of interest or offers on their used boat that looked too much like a fixer-upper, even boats that were in decent condition underneath. (sigh)
And the tired-looking boats keep racking up slip rent and insurance payments, and any tired-out systems stop functioning reliably... which further scares buyers away.
Obviously, this is a one-cent opinion, after the usual discounts apply.
ps: the Ericson in reply 52, looks like a handsome & debonaire version of a "wolf among the sheep" !