Do you want to take pics, or just stargazing? You want to be mobile or just in the back yard?
I'd get a Dobs if it is just start gazing in the back yard. A big one. If you want to move around that's different. Though I don't think it would be a problem for you to carry a dobs, POP. It's for me, lol. But if you are going to take pics, as you know it is completely different thing.
In my experience, I have found that the crude-simple designs are the most fun. I mean chasing the objects by yourself is better fun than going with a computerised one. But I don't have any telescopes myself. Limited experince.