Hi Ben,
Welcome aboard,
One of the best scopes I have looked through is an Orion 14 inch truss tube Dobsonian.
Read Rick Petrie's review in the equipment review section.
His is not goto, but they have since released a goto version.
Around $4grand from memory (don't quote me).
My favourite astro binos are Orion mini giants 9x63.
From Bintel.
They blow the rest out of the water in my opinion.
And yes a good tripod will definitely be an aid for even the lightest binos.
With so much of your bank left over, you could then buy specialist astrophotography gear when that takes your interest.
In the mean time, dont compromise your visual observing by buying something less.
But the recommendation to find an observing group near you to see the gear and what you will see is the best advice to give you.
Unfortunately you will not be able to see the quality visually that you see in the astro photos.
These require an open lens for hours to collect all that light.
No available telescope will be able to deliver that amount of photons for your eye to process to achieve that result visually.
But none the less, there is a special sense of "conectiveness" that visual observing gives that is missing looking at pre recorded photos, no matter how wonderful they are. (IMHO)
Good observing
Allan