Dude, you really did go off the deep end.
I'm 49, took 23 years off of riding while my wife was terrified of me dying and leaving her with 5 kids to raise alone. But I had ridden before, mostly small dirt bikes or touring bikes (a KZ1100 with a Windjammer, and full bags was my last bike to sell back then), there is no damn way I would have taken on an Africa Twin starting up again, and hesitated on the KLR. You either have lots of guts, are crazy or both!
Anyway, it sounds like you have money to fully equip, so here is my take...
1) decide how you are going to ride, that is are you commuting, touring, or riding around locally? I'm planning on far touring about 2k miles, but won't do that until late summer 2019, currently, I'm just getting my legs back, working up for 2-3 hour rides (mines a 98, intentionally because I'm planning on abuse that would kill me on a newer bike, and mods to change it to my purpose rather than inside the box.) As such, I've fabricated a skid plate and crash bars (were farmers, so some things are not pretty, but we can just about weld up anything), rear side guards for some soft gear bags/panniers, but that's it currently. I'm torn between doing a backrest or buying one, but currently, we're just figuring out what mods to make.
All that being said, I'm currently running a milk crate with a bunjie net for carrying my little bit of stuff.
I will say that when I stumbled into the KLR I had been looking for a V-Strom, but only because I thought it would be better getting me close to the dirt I really wanted to ride on, but having added 2000 on the clock to the KLR the only thing I think I will be figuring out how to add is cruise. But I will be changing to a less aggressive nobbie as these are great on loose dirt and mud, but they suck on gravel, in fact gravel for some reason makes ice look easy and if it's really loose/fresh I will take the ditch rather than the road to be safer.