Welcome to IIS adds
In this case I think I would suggest the standard start into astromony. For your $1000 get a 8-10" dob, get to know the sky visually then later when you have some more money add a HEQ5 mount to this setup for the photography part of your hobby.
The best advice I can give in this hobby is to make haste slowly. Get a good basic setup, add the accessories you need (collimating eyepiece, red torch, planisphere, chair, Telrad, good eyepieces, remote focusing) then get into the photography bit MUCH later when you have more understanding.
Maybe not the answer you wanted but good solid advice IMHO.
Cheers