Tromper, I've kinda said some things above that pertain to what you've told me.. I do like the RV200, the HD kinda and I've looked at the SMAX also which seems like a good bike as well. I feel like if I go any higher price that 4k, then I don't really see the point of getting rid of the DR650. I can spend 800 on new wheels and tires and have a supermoto that weighs what the big scoots do or less.
Deep down, I just want a small little bike. I had a TW200 before the DR and that little thing dragged me around all over for a year and a half (even hitting 70mph a few times!). I guess that is why I like the Fiddle III, Like 200 and if all else fails something like the RV200, SMAX, Burgmann 200 or used burgmann
While a DR650 with SUMO wheels sounds like fun, you can't beat a scooter for practicality. It's not just the weahter protection. Having all that storage will spoil you. My record for hauling groceries on my little Super 8 is $87 worth form Wally World. I could easily haul a lot more on my Majesty.
As for the big vs small debate, both have their advantages. Small scooters are silly fun in a way that bigger scooters and motorcycles can't match. I have owned a lot of bikes and ridden hundreds more. Nothing I have ridden is as much fun around town as my Super 8. Bigger isn't always better. This is coming from someone who has owned 1100 and 1200cc motorcycles.
However, a smaller scooter is limited as far as where you can ride it. I have never ridden my Super 8 much more than 200 miles in a day and seldom ride it on the interstate. When I replace it I will be looking for another small scooter with just a bit more performance. Of course I have three bigger bikes to choose from when I need something bigger.