Hi Chris welcome to IIS
Congtratulations on being in a position to get a really nice scope. There are many pros and cons to any telescope purchase simply because there is no such thing as a perfect alround scope. Everything is a compromise.
I am a dob user and don't use go to or push to technology, so I am probably biased. However my usual point is that if you go to any star party and have a look at what people are using, by and large the majority of visual observers are using dobs. Simple as that.
The 8SE involves sacrificing aperture for the convenience of go to and if you really need to have go to then go for it. To me, I enjoy the hunt!
For your budget you can have a 12" dob with twice the light grasp of the 8SE and still have $2k left for accessories, especially good eyepieces, atlases and dew heaters.
Your other point is astrophotography. This is an alt az mount, so is really only suitable for bright planets and the moon. Deep space will require (usually) an equatorial mount. There may be a way to wedge this mount, but I am not sure.
Malcolm