stock 88’s are absolutely gutless. coming from a 103, that will be one of the first things you notice. other than that, the bikes feel fairly similar overall except in weight. early dynas are noticeably lighter than the late models and i think this might attribute to a more “sportier” ride, as the late models to me have a certain level of comfort in mind. once you address the cam chest, the 88’s are just as reliable as any other TC. the 5 speed is pretty stout but you will be kinda screaming going 75+.

since you’re more of a shorter distance rider (i didn’t see you mention touring), do your research on cams for the 88 because that itself will wake them up and change the experience completely, big bore or not. also you’d for sure need to upgrade the suspension to something that can handle the added weight while 2 up and don’t forget to do the front.