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Just make the appt. for the service a few days before your trip and get as many miles in as possible before you take it in. As long as you are close it won't matter. I would at least get the oil changed if nothing else.
If you go 300 miles over 1k before the service, no big deal. The nice thing about this forum is instead of getting advice you get everybody bragging about how many miles they ride. I'm really impressed.
I would at least get the oil changed. Reason is, there is going to be casting flash and other little metal particles in the first oil change. I would do the first change at 20-50 miles after several 2000-4000 slow roll ons allowing the engine compression to slow it down each time. (of course allow the engine to warm up to propper operating temp first) This will allow the rings to begin to seat. Then I would use the dino oil until the 1000 mile service. Just one opinion on break in.
I'm a "suit" as well. I commute to work everyday on the bike. The Army requires that I wear boots when riding on post. I wear my normal work clothes (usually just slacks and shirt with tie - sometimes a jacket) on the bike with the exception of shoes. I wear my boots to ride and have spare shoes at the office. There are times that the slacks (because they are so light) ride up and look dorky. To solve that, I simply found some mattress clips (they are made to hold a sheet to a mattress) at Wally World and my wife sewed some elastic to them to make stirrups. Clip one side to the slacks, run the elastic under the boots, clamp the other side. Works for holding the slacks down so the wind doesn't blow them over my knees - with black elastic nobody even notices the stirrups when I ride past.
My bigger concern (rather than the 1,000 mile service)would be trying a 1000+ mile trip in three days without working up to it. I do several 1000+ mile trips a year. I work up to that first one of the year by doing 100 - 250 mile Saturdays and Sundays for a month prior just to get the back side used to the saddle again and to get the wrist used to holdingthe throttle for prolonged periods of time without going totally numb.
Clock as many miles as you can on it and get it in for fluid changes and a once over.
Granted the manufacturing processes for building engines that have not significantly changed since moby dick was a minnow have gotten better, meaning the engine parts are machined to closer tolerances, and the assembly processes are a lot cleaner, you still need that first oil change done at 800 to 1000 miles, AND you need to make sure the nuts bolts, forks, swing arm, brakes, etc are given the once over by someone who (we hope) knows WTF they are doing. The oil will not turn into molasses at 1001 miles, but do really want to trust your 3 day ride, your safety, and the safety of those around you to fate? Get the bike given the once over, granted the trained apes at the factory, and the 8 dollar an hour recent MMI grad that uncrated it an did the prep should have caught everything, but I have seen all makes of cars and bikes with scary things at low mileage that if they were not caught early would have been catastrophic in failure.
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