http://boston.craigslist.org/gbs/mcy/5110312064.html
http://boston.craigslist.org/gbs/mcy/5057665643.html
http://boston.craigslist.org/nos/mcy/5101709564.html
Just some examples, Chevss. The third one is a Road King, more of a touring bike, very comfortable. These prices are definitely higher than any of the Jap bikes, but nowhere near what they were three or four years ago. Used prices have dropped dramatically.
Maintenance: Not so much with Jap bikes. Harleys, somewhat yes. If you get a good, clean bike, you shouldn't have many problems. Harleys are much improved from the shovelhead engine days when they leaked, misfired, and broke down all the time. One of my bikes is a 1980 shovel, a stripped down police bike that I turned into a rat rod...I love it, but it's old school as hell.
The lower mileage bike trumps a newer bike for me every time. With Harleys, I wouldn't look at much over around 20k for miles. Most people that ride Harleys have great respect for them and treat them well, take care of them, because they're so expensive. Jap bikes, like anything they make, tend to run clean for lots of miles. I like the Kawasakis, though they all have a good record for endurance. The Nomad is a fantastic bike, great looking, especially the model with the hard bags. My husband thinks the Nomad is one of the best-looking bikes on the road with a lot of bang for your buck and short on maintenance.
If you do go with a Harley, don't listen to anyone telling you that the twin cam fuel-injected engine is the best thing since chocolate cake. It's not. I would much rather go with a carbureted engine. Easier to fix, cheaper to fix. The newer twin cams from somewhere around 2005 on up have a 6-speed tranny, and unless you're planning on riding out to Sturgis with the bike, there's no need for that.
I'll be interested to know what you go with. If you find what you're looking for and have any questions, ask away. If I don't know the answer, my husband will. Good for you, by the way! You only live once!