My current astro journey has taken me down the dob path, slowly acquiring all the bits i need.
so i started off with a dob till i could afford a mount to run it on. it came a little sooner than later so this week i pick up a eq6 pro. so now i have a 10" dob with full tracking abilitys that will stay as a visual rig until i get a guide scope. to which i will then get the guide camera and then a dslr. I got away with the whole set up very cheeply as i saw today that a 250mm skywatcher with a eq6 mount was close on 3500, yet i have just cracked the 2000 mark.
Like everybody who is into the photography side will say and just like monoxide just said, theres no point to getting something that will only just handle what you have now. Its a fact that you will want better and better equipment untill you cant get any better without going professional.
By all means try to make the entry into it as painless to the pocket as possible but yeah. your choice