Awhile back some one was looking for a Harley with a $1500 or $2000 budget.
I had never seen one for less than $3500 and now it's time to eat crow!
1988 Sportster 883, in Knoxville craigslist for $1800. It does have a problem with title. Guy bought it from a storage auction but I would think with paper work from the storage facility you could get it titled.
Also saw one for $2850 this week, so I guess there out there if you look long enough!

 

Cheapest I have ever seen was 2500, for a 94 Sporty. I am sure you could find an old rust bucket for cheap but if the bike is road worthy or just shy of, forget it. IT's going to cost.

 

Here is the lower midwest I've seen a number of Sportster going for in the $2,500 to $3,500 range.

A friend of a friend has a real nice 1980 Ironhead and he is asking $3,000, but I've been told that he would take less for a cash sale.

http://kansascity.craigslist.org/mcy/1609382177.html

I like the old Ironheads, but I need another bike like a hole in the head..

 

Sportster HAS to be the best MC value around. just sayin...