Some years back I decided to treat myself to a telescope, a bit of an indulgence really and though I've not used it a lot I'm really glad I got it. My circumstances were that living in a city it had to be genuinely portable so I took it with me on weekends away. I bought a very high quality 4" appo refractor. If I had dark skies at home I'd have bought an 8 or 10" newtonian. Newtonians are I gather by far the best bang for your buck. Apparently these are inherently better optically and certainly a lot cheaper than the compact and more portable schmidt-cassegrains from Celestron and Meade. On thing though is to budget a goodly sum on the tripod, maybe as much as on the telescope. This sounds silly, but having tried to make do, I ended up buying a really good tripod in the end and it was very much worth it. Remember to budget for a couple of good eyepieces too.
Having said that, some of the Dobsonian mounted newtownians do look like amazing value for money. I've not used them but basicially you have to nudge the scope round to the target rather than twiddling the knobs. Dunno how tricky this is. Might be a cheap way to get a biggish scope and see if you want to spend more.
Anyway, in your shoes I'd look at 8 or 10 newtonian from a respected make, either dobsonian or proper tripod according to budget. Keep a few hundred for a couple of good eyepieces, or if you've got the dosh £1500 for 3 or four super dooper eyepieces.
