I grew up on the series, with the first game being my introduction to the next generation. Volition developed one of the most underrated open-world settings, in Stilwater with the city being a major character in level design. Nothing was placed in the world for no reason; bowling statues can be knocked over with cars and online was fleshed out.
But SR2 redefined the franchise, giving it a strong personality with wacky and fun tonal balance. Everything about the game was perfected after the first game was a bog standard open world game. It added characters we cared about, made the side activities worth completing and giving the player tools for distraction without slowing pace. Despite having awful driving controls and mediocre graphics it trumps any GTA game releases since San Andreas. It sad what happened to the series eventually, as volition forgot what made the original games so engrossing.
So to answer the question OP, of course, it deserves a remaster. Maybe even a reboot set in Stilwater would be enough for me. I would also welcome a backward compatible patch on the Xbox One.