What do you think might happen to your chain bolts in 250 miles? I rode across the country with 12 other people. That represented over 44,000 bike miles. Not one chain bolt problem. Not even one chain problem.

As for off-bike clothes, get a synthetic t-shirt. I have a Dry-Fit one and an UA one. I will never tour with a cotton t-shirt again. The North Face makes a light pair of convertible pants (pants with zip off legs). Get a cheap pair of Dexter sandals from somewhere like PayLess. They are very light. Anything else will be climate-specific. For example, I just got back from a three-day. I brought a wool hat because the nights were supposed to get down into the upper 30 to low 40s.

And you don't need touring-specific riding clothes. I tour in the same bibs, arm warmers, leg warmers and jerseys I use for road rides. The only thing different are the shoes. Touring is nothing more than riding with some gear for after the ride.