Hi Chris.
Yes, you can read and read and read and still not know which direction to go.
The easiest answer is get a big Dob, and up to 10" they aren't very hard to move around or transport in a solid tube arrangement.
But now with the proliferation of Truss Dobs and folding Dobs you can go much bigger and have ease of transporting them.
16" folded down will fit in a small car!
But you want to do a bit of imaging?
Lunar/Planetary or Deep Space? They both require different specs.
For Lunar/Planetary you can do with a webcam etc and a Dob.
For Deep Space Images (DSO's) you really need tracking and more importantly, for longer exposures, you also need Guiding.
I could suggest an ED80 on an EQ5 or HEQ5 as a good starting point for imaging, but that will take you over budget.
There are GoTo Dobs now that are great. You'll have to check on prices for those. They will allow short length Long Exposure images and easily do Lunar/Planetary imaging as well as be great for visual work.
Your username (skuppy) will always sound like a New Zealand version of a Kangaroo to me