My opinion is that you should think hard about what you want to do first in the hobby before spending the cash.
The reason I say this is that many of us have multiple scopes for different purposes, visual or imaging, etc and I feel it's important for you to buy now what will be a catalyst for your enjoyment of the hobby going forwards.
Personally, I could look at the planets and the Moon and brighter objects that are visible from suburbia every night of the week if the weather would cooperate. It never gets old
In which case an 8" Dob would serve you well and leave you a little left in your budget for accessories.
Don't get too hung up on high magnification...those nights are not the norm and you'll have built up experience and will have learned to deal with it when the time comes.
If you're more interested in the imaging side, decide what sort of imaging you'd like to do. You can get started with wide field using just a camera and a lens. A tracking mount lets you take longer exposures. Then you can add a small telescope for zooming in, and then additional scopes to increase the focal length to tackle smaller objects. The universe is your oyster!
Almost everything in this hobby involves opening our wallet...space travel costs money
