I rode from VA to Toronto to Oshkosh WI and back to VA. I picked up a joe rocket tank bag a couple days before I left (it was all that was in stock at the local shop, but seems to work ok) and straped my book bag to the rear seat and that worked well enough for me for the next week. Put soft stuff in the tank bag so you can comfortably lie down on it. Pack fairly light and be careful that nothing could possibly get sucked into the rear wheel.
I've never used a cruise control, but there are models that replace your bar end and seem to work ok. Bring a little chain lube with you, tire plugs and something to air tires up and check pressure.
I left VA around 4pm and arrived in toronto about 1am (~650 miles)
left toronto about 8am and arrived in madison WI about 6pm (~800 miles)
left Madison around 7am and got to oshkosh around 10am I think. (~200 miles)
Stayed in oshkosh for a few days (eaa air venture)
Left oshkosh aroudn 7:00am got back to NoVA around 10pm (over 1k miles).
The main thing is to ride and have fun, the equipment doesn't make much difference imho
