Hey Tim,
to IIS.
Good advice on the binos, I've got a pair of 12 x 50's and 10 x 50s and they're both used a lot. Hiking out will give you dark skies so you will be surprised at just how effective they are. Also they won't embarras you.
My 'Grab & Go' is an Skywatcher 80mm f5 Refractor, used by many as a guidescope. That and a photo tripod mount, 2 EPS and a dark sky will give quite amazing views and still be useable even in the suburbs. Be quite a bit heavier and cumbersome than binos but a lot less than an 8" Dob. There are several brands, Orion, Meade etc etc all the same spec ( and same factory I think) and price is wihinm your budget. Check out the Bintel website for package deals new. You may not need the supplied mount or it could be useful at home. They have
Just another idea