Yeah, you're gonna have fun.
With these old bikes, knowing how to turn a wrench or having the aptitude to learn how to is a must. It's close to the end of the riding season, so I would enjoy it while you can, and then dig into her over the winter doing some of the high-mileage maintenance stuff and fixing anything you may turn up when you're riding. If you don't want to work on the bike, don't even buy it. Things will go wrong, and taking it to the shop is not an option unless you're made out of money.
Give yourself an extra 5 minutes of "inspection time" every time you're about to take it out. Use this time to give the bike a good once over. Check your signals, tire pressure, chain tension, clutch cable, oil level, tire wear, etc. Bikes need more attention than cars.
Grease your chain about every 2-3 rides. I like the white lithium type grease that sprays on thin and sets thick. Find out if you have an o-ring chain, and if you do, make sure that the lube is safe for them. Some spray on lubes have stuff that will break down the rubber o-rings.
As far as riding the thing, don't be afraid to lean. As someone said, don't cry when you lay it over, because you will. You've got highway bars, so that should help. I wasn't so lucky and shattered my pickup cover. If the bike has points, I'd recommend changing to a dyna electronic ignition when you have some extra scratch. Make sure you're comfortable with the bike before you take a passenger, and when you do take a passenger tell them to lean with you and don't squirm unnecessarily.
Of course, my first inclination was to say ditch the sissy bar, take off that exhaust and throw a 4 to 1 on it.
Getting a motorcycle on Monday....
