You guys are all way out of my league, so I certainly don't have anything to teach. But, I've found a lot of useful info in forums like this so I'm going to post my experience to help contribute to others that may want to try something similar.
I had an '08 KLR that I'd enjoyed for a few years but had recently began to feel like it was just a little too tall for off-road fooling around, and a little too nice to boot. I was doing less of the touring it was great at, and more running around town, short rides, with the occasional trip down a gravel or forestry road. I like the look of 70's cafe bikes, but wanted something a little rougher and tougher. I'd had a 74 CB200T that a guy had redone but it was just too weak to enjoy. Still I wanted something that wasn't too heavy if it was going to be my version of a scrambler.
So I came across a 1983 Nighthawk 550 on craigslist, and owned it by the following morning.