I ride alot and 250 miles is nothing for me. But I do ride a touring bike. My opinion would be for some thing in the FX line and not a softtail. The softtails look great but suffer by design because of the rear shocks. They have to be smaller to be hidden under the frame. The FX's have larger shocks mounted outside the frame. If you like the softtail look check out the Wide Glide or the Fatbob. But everyone's opinion is different. I do know people who ride long distances on a softtail and love it. To each thier own!
The Dyna line rides better due to the rear suspension frame geometery,the softail are intended to replicate the rigid or hard tail bikes of days gone. The FXR line was HD`s best handleling bike which isnt made anymore. It had the swingarm mounted rigid in the frame not the rear of the engine case like the later FXD series and subject to motor mount flex and wander,which can be cured a few ways if you wanna spend the bucks. As mentioned dont be afraid of a EVO bike,better mileage,no cam issues,mass aftermarket etc.
Go rent one of each and feel the difference,its cheaper than buyin a bike you end up not liking. Looks go so far then you`ll realize your screwed,not sayin the softail line is bad,just different. I have no problem riding my my 93 springer softail 500 in a day,if I was in need of speed and more miles the FXDXT does it. I sold my bagger,great for long distance in crappy weather,not much fun in the twisties.
Bikes with the tall skinny front tire aren't quite as comfortable on a long ride, but admittedly they do look cool. Touring bikes have beefier front and rear tires with more sidewall which increases ride comfort, but sometimes comes off as a paw paw bike. I think the Heritage Softail does a good job of splitting the difference by having a softil frame with the hydraglide forks with touring style tires. Mine is pretty much bone stock. It's a 95 model. I bought it last year with only 19,500 miles for $8,000. It runs perfectly and has only needed a rear tire and a brake job. NO LEAKS OR ANYTHING. I flew to Atlanta and rode it home to the Lafayette, Louisiana area. It did fine on that trip. It also works great around town.
__________________ 2014 Copperhead Pearl Unlimited Sahara in progress