5 years ago , i would have said : go for it ! 2000 Classic , winglets proline 21, the whole package, yes !
Today not quite, the economics have changed , the Classic starts to age, and you will find an Easy for that price, with better engine performance, some new systems, a taste of "tomorrow"...
I am sure that your classic works fine, and to be honest i flew falcon 20 retrofitted which are flying like a charm at 40+ years old ( the airframe).
So except for budget ( acquisition) concerns, i would not buy a Classic today.
( as far as the CL30 is concerned, i am not flying it :-) )
ho , yes winglets.... hmmmm... keep them off the plane, hangar, towing, lens cost...are the books reflecting the ground performance now ?
But again, this is my one and me only opinion; everyone has to make a decision otherwise everyone would go for a B747-800.... or an ultralight...