i was traveling home today from visiting family and saw tons of Harley's and a good number of them seem to be Sportsters. I know they fall under cruisers and aren't sport bikes but do they or can they be made to handle or are they pretty much straight line bikes?
I know this may cause some flake but Sportsters are probably the most nimble Harley. Lighter and smaller. After all, there must be a reason that Beull used it as a base for his.
Actually, I had a discussion with a H-D service manager who said the opposite; the Sportster doesn't handle all that well compared to the larger bikes because the bigger ones have a better center of gravity/weight distribution.
What I do know about Sportsters is they are essentially the training wheels or gateway drug to the bigger/better hawgs. Very few people keep theirs once they can afford to go bigger. Every time I total one at work, the owner does not replace it with another. They are not the most pleasant to ride, apparently, with lousy ride quality and mediocre handling. I think this is reflected in their lackluster resale value. For the price of a Sportster, you could buy a bigger, better Harley pretender like a V-Star...and avoid the need to spend another thousand or two on H-D branded merchandise. 
I've owned 96 and 05 Sportsters, have ridden big twins, and currently own a Buell. Of the cruisers Harley makes, the Sportster is the best handling bike, but that's not saying much. I'm excluding the XR1200 which is supposed to handle well, but I've never ridden one and it's not really a cruiser. I wouldn't go for a pre-Evolution engine (86-present) and I wouldn't go for one before the 5-speed transmission (91-present). The 883s can be easily converted to 1200 with just installing the right easily available pistons and boring out the cylinders or just getting a set of 1200 cylinders. The pre-2004 bikes were solid mount, the 2004+ bikes have rubber mount engines. The rubber mount bikes weigh about 50 pounds more than the pre-2004 bikes. The pre-2004 bikes have more vibration through the bars, but I think mine felt stiffer and handled better. My 05 had less vibration through the bars, but feeling the engine vibrating out of sync with the rest of the bike against my leg was really annoying. I might be in the minority, but I prefer the pre-2004 Sportsters. My 96 Sportster's brakes weren't that good and it didn't handle all that well, but I liked it for what it was and enjoyed putting 8,000 miles in 8 weeks while riding around the country.
Buells are not really based on Sportsters. More like Erik Buell designed a bike and since H-D owned a large chunk of his company, he had to use one of their Sportster-based engines. Note that when he was allowed to deviate from Sportster engines with the 1125R and 1125CR, he designed and had Rotax build a liquid cooled engine.
They are the cheapest way to get into the Harley family, but with 40 some HP and a design that dates to 1912 or so, they are not great bikes. Any metric for the same price will bring more power and better handling. None are as cool however, I'll give them that.
Evo Sportsters (1985 and up) are a fantastic bike. As reliable as my Toyota RN Truck, and that's saying something. 883 -> 1200 + is pretty simple and cheap, although when I suggested it to Dr.Linda, she said she had plenty of power and leave her's alone (883.) They don't have crotch rocket power. If you want a crotch rocket, get one, or a Buell.
My friend had a '85 883 and a '87 or so Lowrider, considered one of the best handling big twins. He used to race bikes and he said his 883 would out handle the Lowrider. I can't really compare them, as Dr.Linda can ride her 883 better than I can, but then I've put maybe 1K miles on it and she's put > 50K. She put >6K miles on it before we got it home from the dealer.
I would say that a 4 speed bike is just fine. We have no complaints. I hear a 5 speed transmission will just slip in, but 4 speeds is plenty.
My first bike was an '04 rubber mount 883. It was a great bike. Not too fast, not too nimble.... wouldn't get you in too much trouble. Funny thing, I could keep within 30 seconds of 600 sportbikes in a 5 mile section on stock tires and suspension. It mighta been balls or it mighta been stupid, but I did it in a group of experienced riders.
I sold it two years ago because I had too much stuff. I'm looking at DRZ400SM as replacement because I feel like I want lighter.
Turning Sportsters into cafe racers is becoming popular. 883s are relatively inexpensive and handling parts abound. Yes there are cheaper was to build a classic-looking cafe racer, but a Sportster could be intersting. A CB450 would get you as much power and less weight, but that has been done to death. In fact, I am doing one. :o
I still toss around the idea of getting a new 883 Superlow since it has the big 4.5gallon tank and radial tires, adding 13" road king air shocks, respring and revalve the forks, and adding a fork brace for better handling, getting a taller/more comfortable seat and lower bars to fix the ergos... but then I usually think I should just buy a Moto Guzzi V7 stone instead. Still, the stock Superlow I test rode a couple months back was an absolute blast to ride.
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