That's exactly why I'm having so much trouble picking a bike, they're all pretty good bikes. Right now for me the two bikes that have really got my attention is the tw200 and the crf250l. In my area the tw200 and the crf250l both go for the same price new($4999 MSRP) does this make the tw200 less desirable?
I would prefer getting a new bike because i would know exactly how its been treated and would ultimately like to keep the bike as long as it lasts.
This is a TW forum and we all love our TWs, but a lot of members have had their interest piqued by the crf250l, and at least one member has bought one.
I've only ridden the TW, not the Honda, but I've read similar criticisms of both when it comes to performance in the dirt. As has been mentioned, dualsports all balance street and dirt performance in various ratios and with various levels of success.
I'm no daredevil or MX racer, but the TW does 90% of what I ask it to off-road very well. The other 10% is things that require more suspension travel or engine displacement to do well, which would require a higher seat height and heavier bike. If the TW gained the height and weight required to do that 10% better, I probably wouldn't be able to keep up with it for that other 90% of dirt riding.
I would say that the seat height and extra weight of the crf250l are big downsides in the dirt. But the fuel injection, extra 50cc of power, and superior brakes will all serve the bike very well on the street, and for certain dirt riders as well.
I'm rare in this forum as I share your appreciation for the value of buying new, but on a bike like the TW that requires a fair amount of tinkering to get just like you want it anyway, I might consider buying used if I was buying another one. I'm not sorry for buying a new one though, although my out-the-door price was a solid grand less than the MSRP you're reporting for your area. Your Clearance Deals May Vary!
The TW will also be easier to work on, but of course a fuel injected bike will require less work.
You have a tough choice, and the fact is that there is no perfect bike. As motorcyclists, Multiple Bike Syndrome is our universal fate.