I wouldn't over think this much other than starting the ride with your bike in pristine condition and not carrying too much. I wouldn't carry much more than I would on a century as far as "gear" goes. The shipping cloths to the hotel is a good idea or a larger seatbag for extra cloths. If the hotel has laundry you only need one pair of shorts and a jersey and some shorts/shirt for the hotel. You're only riding a 100-135 miles a day or so you're not going to be on the bike very long, if you're in the shape you say you are in. Maybe 5-6hrs? Sounds like you're going to have a lot of down time...I think you should think about doing it in two days instead of five, that's what I'd do.
