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Blake,
Unless you are doing CCD imaging forget about the equatorial mount.
Your best bang for your buck would be a 12" to 16" Alt Az (dob)
Get an argo-navis to find stuff (a decent star atlas is a good way to learn the sky though)
Get one or two good eyepieces, (for an F/5) one of them should be somewhere between 12mm - 17mm focal length. My choice would be an Ethos, but a nagler type 4 or Pentax would be better if you wear glasses.
Also, a NBP filter from DGM optics is pretty much essential.
Before you spend any money though, go out to an astronomy club dark sky night and have a look through different telescopes to compare.
~c
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