The e55 is less reliable in my experience. The intercooler system and supercharger clutch are both failure prone and expensive. Usually with an e55 it's a lot of little problems that are expensive to fix. It also has the sbc brake system which by now, most are out of warranty. $2000 for a supercharger pulley was enough to cure me of wanting one anymore.
The 63 is more reliable with two major caveats. One is the early engines have a nasty habit of digging holes through the lifters and ultimately exploding the engine. The other is the transmission valve body or control unit fails. Providing you buy a cared for example, that stuff may have already been repaired and you'll get a better car out of it.
Driving the two, the e55 has better torque. The 63 sounds better, is faster, and a multitude of other improvements make it the better car. It will likely prove to be less expensive to operate. 7000 rpm is more fun than the neck snapping torque of the 55. They are both fun, both fast. I just find the 63 to be the better car which carries the advantage of simplicity.