Yagon, if you have not seen an 8" Dob first hand you should go to Bintel and check one out because it will show you a hell of a lot more than any of the other options you are considering. Even 6" GS Dob will (but only Andrews have those). They are both quite portable and will cost a fraction of your budget. Spend the rest on good eyepieces.
But if you must have an even more compact scope, the ED80 from MyAstroshop on an AZ3 or EQ5 mount would be very nice. The ED80 is the best of the false-colour-free refractors. And leaves you plenty of change for both must and nice-to have accessories.
If you are willing to put up with some false colour, buy the biggest achromat you can afford/manage from AOE.
Otherwise a 5" Mak + AZ3 or EQ5, or 6" Mak + EQ5. The 6" + EQ5 will leave little or no change for eyepieces and other accessories.
Dob is where my heart is though, otherwise I'd go a 5 or 6" Mak.