I recently went on a dual sport trip with a bunch of guys on their 650 cc bikes. While maxing the TW out back on the highway, my engine died. Still cranks but no start. Inspected my bike at a shop and saw 1 valve has broken, piston was damaged from the valve tapping it. Crankshaft is possibly damaged too. This was possibly due to my poor valve adjustment and pushing the bike harder than it wanted. Labor for taking the engine apart has already costed me $200. I don't think I want to spend money on parts unless someone someone sells me all the necessary parts for a good price to fix it. I'd hate to sell my TW but I already have my mind set on a more powerful dual sport/adventure bike better suited to 80 mph speed limits in parts of TX and CA. Yes, I've done a half cross country trip across the USA before on my TW. I'm surprised it took me that far, from NY to TX and back to NY. I've been eyeing the Honda CB500X for some time now and I wouldn't mind ABS in areas of high car traffic as ABS has saved me in my car. My 1st car was a '91 MR2 with no ABS. That along with a short wheelbase in a dead stop traffic ahead situation has made me spin out too many times for comfort. If anyone's interested in selling me a motor or buying my bike off of me, please comment. Send me a private message with an offer.
To be honest I doubt the crank is messed up. I would throw a new piston and head on it and carry on. Used heads on ebay are about 100 bucks.
I don't see much damage from the pictures. I would fix it and as rbm stated, you'll get a much higher return when you sell it, or not.
Or wait for Gary to get back from vacation, I'm sure he would be interested in a project.
Just sent GaryL a message. Hopefully there's a TW guru who can come by and take a close look.