Having spent time between 500 AGL and FL270, I tend to agree with you. It's a lot more fun to fly low. That said, I tend to fly at the best altitude to complete the mission. That generally means a combination of what altitude will get me the best TAS, efficiency, tailwinds, around weather (icing, storms, etc.) and also taking into account human factors. So I'm rarely flying at 1,000 AGL, although I last winter I did fly from NYC back home to KS at 2,500 MSL (which was <2,000 AGL for most of the trip) because of winds. It was a lot of fun, way more fun than flying at FL180-190. But the 414 is 40 KTAS faster at FL180-190, so guess where I spend more time given my typical 600+ nm legs...
You really have to be going a long ways to get a benefit from being up that high in a piston bird, though. Not like a turbine bird where you get way better speed and efficiency up high.