You are going to have your hands full dealing with the scope itself. This is a tough one to answer, since everyone has their own priorities and preferences. The simplicity part is important, since you will spend your time aiming and observing with your telescope, rather than playing around with the sometimes complicated controls on an equatorial mount. The stereo system which reveals the most music to you is the one you use the most. For most of us, that's our car stereo.
Astronomy is a lot like that.
The probability that a telescope will be used is inversely proportional to its size. This seems to apply to just about everyone, regardless of experience. Little scopes get used more often, and thus show you more. Your Luggability Tolerance may be different from mine, however, and that's where visiting public observing sessions becomes an invaluable experience. The star parties also come in handy when I DO want to look through a big scope.