I mean it is still kind of the same thing... In texas there were tons of people who didn't vote for it... but were effectively caught in their neighbors self inflicted bullshit.
Same concept with blue states... those states may not have had a majority that voted for trump... but the nation as a whole did. (caveats of course for all forms of voting shenanigans, disqualified votes and any possible fuckery with the election itself).
IMO the learning curve for caddy is almost non existent, and just about anything you might want to selfhost almost certainly has a quick simple caddy configuration you can copy paste with just updating the relevant domain. Personally learning curve for caddy was probably way lower than figuring out the edge cases of apache that I was using before