Hi Casey,
When I first started Astro stuff I didn't know what I really wanted. I had a limited budget and made a lot of mistakes. Although these mistake gave me a fast learning curve to optics I think I would have done things a little differently.
I have just recently taken my first EQ shot with my DOB and I can say this without reservation your mount is the most important.
I also found that a guide scope would have been a good idea as my first image of M42 and 43 I took 65 images and was only able to use 17 in the final image. -
http://www.iceinspace.com.au/forum/a...se.php?a=85329
I manually guided my scope so for me it was a good view of the old way of imaging, again I now have that experience and quite happy to experience a bit more manual guiding before spending more money on more complex aligning methods.
Camera, DSLR is a good starter and I use mine for happy snaps as well as AP and it is unmodded. I also use a webcam for planetary.
You have one advatange over me as you have decided what you want to specifically do, so you initially budget can be tide to AP while mine was initially all over the place. I do not regret my path as it gave me an enormous amount of XP and understanding of the hardware.
Good luck with deciding.