it could be pointed out that all the 250's people take the MSF NRC on are big 4 products, but you have a point.
Five year resale value, not so fast. The last time I checked a V-Strom DL650 retained a higher percentage of purchase price than a BMW R1200GS - the GS just looked like it did better because they were so expensive to begin with.
The engine is narrow but the cases are
really wide. I had a Roadster and (ignoring the 3" of rear suspension travel) there was very little cornering clearance. They vibrate in astonishing fashion at idle, they weigh a lot, and the most I ever got out of one tank was 116 gallons. One of my office commutes is 115 miles, meaning I had to get gas every day. Harley spends the absolute minimum on suspension, on Sportsters, anyway. And btw the "Big Twin" riders don't consider the Sportster to be a "real" Harley - it's a girl's bike or beginners bike. I didn't meet a single HD rider who "got" the Roadster (twin disks, tach, Metzlers, upgraded shocks) and in fact the previous owner had lowered it. By contrast sport bike riders were all over it because it was a "functionally improved" Harley.
I visited "there" and the HD culture as promulgated by the $6 billion parent company really is "too stupid for words." The bikes are not as bad as many think in terms of everyday. Reliability and durability and their chrome and paint work is as good as it gets. What they will do when emissions laws kill off air cooled bikes remains to be seen.
Eventually sold the Roadster on eBay. You can't imagine what it is like to sell an HD on Craigslist.