I don't know your budget but from the sounds of what you had issues with in the past, I would recommend something on a sturdy, equatorial mount. Maybe an eq3 or eq4 equivalent, depending on how much crap you plan to stack on the tube. Personally I think backyard astronomy has more to do with learning the sky than pushing a button, and generally recommend learning manual navigation. Besides, something about wires and lights and sounds coming from a telescope somehow reminds me of using whatever newfangled razors are on the Gillette lineup rather than the ease and simplicity of the straight razor

If you're in the city, you can't really expect a whole lot from deep sky objects unless you get a huge scope. Maybe you'd benefit from a longer focal length, SCT or dob that is not terribly expensive for 6" - 10" range. If you plan on using a dark observing site, you can't really go wrong with anything of quality

PS the straight razor equivalent of something you ought to consider is a meet-up. A star party where you can look at a wide variety of observing tools and try them out for yourself to get an idea of what you think you are going to get the most out of. There's nothing like buying something you aren't sure you'd like for hundreds or thousands of dollars without even seeing it in person first