Start by asking better questions - to yourself.
You have a budget, and I wholly understand that, but where is the overlap in money you have to spend right now, and how much pain you will go through down the road because of it. (This applies to both budget, and "biggest monster possible!!" buys)
Ask yourself what you really want to shoot, what results do you realistically want.
(ALL of us want Hubble-grade images from a small scope we barely have to touch, but it isn't realistic)
At some point you reach the limitations of the equipment you have - how soon it is and how difficult it will be to transition will be based on what you do now.
Many people re-sell their original gear here, then move up - as you will notice DSLRs have flooded the classifieds in recent months.
(Good, well-priced astro cameras with APS-C have become available and the original tunes are changing)
Do you have a telescope now? What is it?
An example I have is the ASI224MC - a GREAT planetary camera. Gets good shots, nice sensitivity, high speed - all you could want for planetary. First time I fired it up to point at a DSO I laughed at myself. The sensor is a spec, the FoV is non-existent because of it, and I couldn't find a d*** thing when my mount's model wasn't laser-sharp. After switching it out for an ASI2600MC..... it's a different story.
As for a DSLR - SOME do planetary well, but many don't have a 1:1 pixel sizing, and those that do have a fairly low framerate.
For DSOs, DSLR can take very nice images, though I'd prefer something cooled, even though calibration frames clean most of that up.
(That said, I know there are PLENTY of people taking way better pics than me on DSLR, so up to you)