Given that your only prior riding experience was with a scooter and that was only 20 years ago, I would say that you pretty much fall under the same category as someone who is brand new to riding. That being said…
It sounds to me like your tastes are leaning you more toward the cruiser side of things. Cruisers are great at highway speeds but are cumbersome at “around town” speeds. I would recommend bikes like the F650GS and Suzuki DL650 V-Strom mentioned above, as well as the Kawasaki Versys (IMO probably the best of the bunch).
If, however, you are insistent on a cruiser, I strongly recommend the Yamaha V-Star 650. I would even say that the Honda Shadow 750 is worth looking into but it’s really straddling the line as far as what is and what isn’t suitable for a beginner.