I really would rather avoid getting a 1999 Harley, but there seems to be a bumper crop of them for sale lately. That was the year the twin-cam, 88-cubic-inch engines made their debut in the Dyna family of Harleys, replacing the reliable 80-cubic-inch Evolution ("Evo") motors.
The '99 (and some early 2000) Big Twins are known for camshaft bearing problems. Not every engine of this vintage will develop bearing problems, but I'd rather not play Russian Roulette.
There is a 1999 Dyna Wide Glide for sale on Craigslist in Milford, Conn. I called the owner, who is asking $7,500 for the bike, last night. It has had some mild customization done to it. The bike has about 14,000 miles, but because the seller is the third owner, he doesn't know if the cam bearings were ever replaced. He told me he'd be willing to sell it for $7,000, but, as I said, I'd rather not buy a '99 unless it was really cheap.
Then, this afternoon, I looked at a 1999 Dyna Low Rider that is for sale on consignment at a custom motorcycle shop in Coventry, R.I. That bike, which also has low mileage (about 12,000), has an asking price of $7,800. But it has been for sale for a year, according to an employee at the shop. This bike was mostly stock and fairly clean, but, after sitting on it, I quickly realized I couldn't stand the 'buckhorn' style handlebars, which put my arms and wrists in a very awkward riding position. While I wasn't crazy about the color (somewhere in between purple and royal blue), the handlebars alone killed whatever interest remained in that bike. (Plus, if it's been sitting for a year, the seller probably isn't too motivated to deal.)
At the shop, the employee showed me an older Road King that had an interesting story behind it. The seller had bought it to fix and resell, but it didn't have accident damage - it was the victim of a bitter divorce. The previous owner's wife got so angry at him that she took a hammer to his Road King, smashing the speedometer and several other components on the bike. Although the bike was salvaged, I'm not so sure about that marriage ...