* ramp to get the bike into a flat-bed truck
Haha, that's funny.
With your saved cash, spend $100 on a 20 pound chain of the thickest guage you can find.
And may I also suggest that if the 2 helmets you're getting in the deal are not brand new (never used), that you throw them away. Don't loan them to friends, don't sell them on eBay, just hack it up and throw them out. Anyone that's going to ride pillion should have proper gear as well.
If you're looking to tour as mentioned in the original post, plan on around 1000 for hard luggage and mounts.
Enjoy the ride.