" I have a hard time paying $5-6k for a DR650 with 20yo technology compared to the WR250R." the 20 year old technology is what makes it such a good deal, AND such a great bike. The same thing applies to the CRF230L, with it's simple, air cooled carbureted engine. I admit I didn't like the 230L as much as my XT225, but after seeing the third world made, poser CRF250L, with it's "new technology" I would gladly pay the $500 more for a Japan made CRF230L. Unfortunately that choice is no longer available.
I won't spend more on a bike than I think it's worth, but if it's a good deal, I don't seem to have a problem buying bikes I don't need.
2002 Vulcan 750, 2013 Royal Enfield B5
2001 XT225, 2009 Genuine Stella
1980 Puch moped