I blew up my engine on my 2005 earlier this year and my wife found a new TW for me. When she asked me if the TW is really what I wanted, I did hesitate for just a second thinking of the XT250. I just couldn't do it though and got the TW.
When I bought my first TW the XT was still 225 and I didn't think the slightly more cost was worth the extra 25cc. This time I have no excuse like that. I've just plain fallen in love with the TW. I feel guilty when I ride one of my son's KTM. Loyal to the TW I guess.
Hope the TW fills the gap between the TW and Rebel for you.