In your replacement bike research, give the Honda CB500X a look - if you're not set on another Wee. Having had both, either would be an excellent choice.
If you're looking to be more comfortable off pavement, the X is much more dirt friendly. I put 50/50 tires on mine and felt very comfortable on anything other than goat paths. It WILL do highways: I did a couple trips to Nova Scotia on mine. You just won't have the power reserve you would have with a Wee. Fuel economy is 65-70 mpg.
(There are so many great bikes now. It's just a matter of what floats your boat and stirs your soul. For me, that's my Tiger800XRx as I have a 250 dual sport for dirt work.)
'11 white Wee "Big One"
'03 BMW yellow F650GS "Roadster" sold
'08 Audi A3 S line Tiptronic
"When you talk, you are only repeating what you already know. When you listen, you may learn something new." Dalai Lama