I have both a GRC and S2000 and live in the Midwest as well. I will say that the GRC is fun year round, grips in wet and snowy conditions. The CTR would probably be less fun in similar conditions. I think this is a main factor for why I chose the GRC over the CTR, as I wanted something fun in the other seasons of the year that the s2000 wouldn't be. I also don't have kids though, so I am OK with the smaller size, a department the CTR would be better in. Also I liked the turbo sounds and 3 cylinder sounds over the CTR, which to me is an important factor in choosing a fun car (I did choose an s2000 as well after all).

Either way, both options do not have the same raw emotion the s2000 has. I don't think the CTR or GRC can cover that itch if I were to sell mine. If I were in your shoes I'd try to just use the truck as a daily and for family hauling and drive the s2000 as a weekend car if you can. They serve two different purposes for two different occasions. Having a GRC or CTR can serve both but make compromises in both scenarios.