G'Day Jason
Welcome back to the hobby (obsession)!
I wish I had all the answers for you, but alas I don't. The holy grail of the one use for all (visual & imaging) scope is something that still alludes me!
I am gathering from your discussion below and situation that portability is key!
Based on this you could consider:
EQ6 Pro/Orion Atlas with a 8 - 10" Imaging Newt, 8" - 10" SCT with focal reducer or a 4" - 5" APO Doublet refractor. Albiet you may have to do some searching on the classifieds to keep within budget (especially the refractor option).
Any of these would be a great package for visual and imaging, however all would be a pain in the butt (SCT & Refractor not much so!) for trampling up and down sets of stairs.
If you are looking for something that is truely portable, maybe the following:
HEQ5/Orion Skyview Pro or a CG5 mount (this mount will have a limited load capacity of around 15 - 17kgs) with an 8" - 9.25" SCT or a 4" - 5" APO doublet refractor.
This would be a lot lighter than the EQ6 and a Newtonian and more transportable, especially if packing into a car for dark sites. The thing to remember is that you will be limiting yourself more to the scope you can use in the future due to its lower load capacity than the EQ6 Pro (which its approx 25kg load).
The thing to ask yourself is what kind of imaging you want to do (planetary or DSO)? SCT would be great for planetary and with a 6.3FR will be ok for DSO (I have seen some good DSO images taken with SCT's checkout google images). Where as the 5" APO Doublet (something like a Skywatcher 120 Pro, I wish I could have one!) will be great for DSO's and good for planetary.
The SCT (or a MAK if you are looking at just planetary) & APO Refractor will be better options for transportability, holding collimation during travel, easier to find/build cases for etc etc.
I worry in that you will not be any different to any of us, in that once you get back into this you know the "aperture fever" will take hold!
But sometimes you have to make trade off's (i.e. money, space, quality of light polluted skies etc) and go for a more suitable option!
I think if you were to get anything too heavy and cumbersome, you may soon put yourself off and the equipment may see little light.
Good to see that you are not rushing in and taking time to consider though.
Best of luck
Regards
Gav