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Hi Carlton.
I've sort of just gone through the same process - I recently bought a telescope after not having owned one for many years, so it was sort of like the first time.
If you can get to a local astronomy club I suggest you do go along and have a look through some different telescopes. It will not only edumicate you to what you can see with a given type / aperture, you'll also be able to chat with their owners about what their telescopes are like to live with.
Other than that I'd suggest having a think about what you want to look at (ie, DSO's / planets / the sun etc).
Also give some consideration the the mount type, eg, Dobsonian, equatorial etc.
After recently taking up visual telescopy again (as mentioned I haven't had a telescope for many years), I'm remembering the things that frustrated with my first telescope (a 4.5" Tasco Newtonian). Like, at high powers things JIGGLE a lot, and they move out of the field of vew quickly. And DSO's can be really hard - sometimes impossible - to find. Looking back, that telescope was pretty small by today's standards. For visual observing I'd certainly be leaning to at least 6" aperture or more - budget permitting.
That said I spent many a happy night under the stars looking for things, and there's nothing quite like the thrill of finally finding one of those elusive little buggers you've been looking for.
So have a think about what you want to achieve, and where you want to achieve it; the ability to travel to a dark sky site can be a real bonus.
Above all, to pinch a phrase someone else coined: the best telescope is one that you use. In other words don't bite of more than you can chew with a first scope.
I certanly hope the above somewhat rambling discourse gives you some insights and assists in some small way.
Happy photons to you.
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