Thanks for all the suggestions, everyone! Ya'll are a great bunch, you really are.
I'm still not sure about what I will do. I'm going Friday morning to remove my personal items, electronics, etc. I will snap photos at that time!
I'm leaning towards that black V-Strom for $6000. I know the seller and I know it's a well maintained bike. It's also completely 'Dustinised' already and I would have to do nothing to it. He's done everything I would do to a bike; emulators in the forks, full Givi bags, crash guards (hahaha), heated grips, aux power, GPS mounts, Pilot Road 3s, centre stand, etc...
I'm wanting to do some two up riding with the girlfriend next year and this would be a great bike for that. It also has the advantage of saving me $400 a year on insurance and $300 on fuel or so. That coupled with great distance comfort & wind protection and over 300 mile range kinda sells it for me.
I've never been to keen on the V-Strom but this is an opportunity to challenge my bias and experience something new. I've heard they are capable handling bikes and it turns out it's only a few pounds heavier (wet) than the 919 or a gen 2 FZ1
2009 Vstrom 650 ABS