Hi David and a big
to IIS!
You are certainly doing the right thing by asking for advice before spending $$$. The moon shot is very good BTW and just shows what can be done without specialised astro gear.
Unfortunately $1000 is a fairly small budget for getting into imaging but the good news is it will go a long way for Visual use. A 12" dob can be picked up for well under that figure and that will keep you happily observing for years.
Please bear in mind that imaging gear and visual gear are largely exclusive. Almost all serious visual observers use large Dobsonions these, and when I say large I mean as large as they can afford, if your budget only runs to an 8", then that will still give you views of thousands of objects.
I would suggest you research clubs in your area or any astro camps coming up that you can get to. Once you see some of the gear actually being used it all makes a lot more sense.
Malcolm