The other elephant in the room is how much you want to spend. It is possible to do decent planetary with a webcam and almost any scope, but deep sky can turn into a bit of a monetary black hole. If DSOs are on the radar you need to do quite a bit of research on quality mounts, scope to give a decent flat field, and guiding options.
It is possible to do some planetary work with later model DSLRs by collecting video too.
Plenty of helpful souls here to bounce ideas off during the wet season though
