8 inch dob gets my vote for ease of use and cheap, having come through the expensive route myself. Or even cheaper, banana lounger and some binoculars, spend the rest on a star atlas, a red light and some fine ale....plus mozzie spray.
If you want to go down the photography route later-it's easy to sell as Brendan says, plus you would now know what you want to photograph.
Here's my case study
I have owned (in chronological order over a few years)
6" newt
Meade ETX
Meade LX 90 8"
Meade 80mm refractor
SW 100mm refractor
GSO 10" newt
SW 8" Newt
Do you know what scope I use most, and use for photography? the 80mm refractor.
I still own the last two newts and they are great for planet/lunar stuff but my skills aren't up to others on this forum for alignment etc so I find the small refractor much easier to align, guide and use with my standard DSLR.
As folks have said, go to a star party, find what you like then buy.
The SCT's like the Meade with GPS etc are truly excellent for visual and for impressing the friends, but photography is really hard with them as the fork mount limits exposure and the long focal length really means spot on alignment if you fork out for a wedge, people do it, mainly on a pier I think.
Go cheap and resale-able, then decide if you want to dive head first in to this great hobby.
No one on here (this forum) I think regrets it, but then they have girlfriends/wives/partners who probably think that $2000 could have been a holiday or a new microwave or some personalised hankies etc.
Personally, my wife has no goddamn Idea how much I spend on astronomy!
If you buy second hand, there are a lot of people here who will help you out.
Sorry for long message, it's still not dark and I have everything set up!
Had a couple of beers too, -didn't kill that Chook though Brendan, do you think my guiding will be ok tonight if I just scuffed it with my boot and snarled at it?
Here's to swimming with bow legged women!
Graz