As one noob to another I will tell you of my experience with my 8" Dob. I have only had it for around a month so I am hardly an expert in matters astronomical but I find that by using aides such as a good star map (the one in the AS&T magazine is quite useful), a computer program such as Stellarium and the good ole Binoculars make finding objects a little easier. Learning some constellations and brighter stars also helps.
I find my scope will give a reasonable view of solar objects and some DSO's (I'm still awestruck by views of The Orion Nebula,Saturn and 47Tuc and return to them frequently
) I'm in a pretty light polluted area and haven't been able to try it out under dark skies so I'm hoping for even better views when I finally get a chance to do so.
My only regret is I didn't go for a larger scope (yes, aperture fever has hit me already) My 8" is easy to move around and I think a 10" wouldn't be too much more weight to lug about.
As for the budget, mine was similar to yours. The actual scope wasn't that expensive but now I'm starting to buy the accessories which are quickly becoming more expensive than the Dob.
My advice, get a Dob and work your way up from there.You can't go wrong I'm sure some of the more experienced folks will have lots more advice. They are a very helpful bunch indeed