The sportsters come in 883cc and 1200cc in several diffenrent packages. The biggest drawback are the peanut tanks that you will only get about 85-100 miles out of. To me, they are a little uncomfortable to ride. When you ride with other guys they will get sick of pulling over so you can get gas all the time. Easily remedied with a bigger tank, but nothing, NOTHING, that you do to a Harley will be cheap. On the bigger Harley's, the EVO's - The 80 inch evolution engine is 1340cc but only produces about 54 horsepower. A typical "rice-burner crotch rocket" at 1000cc will produce about 100-120hp. So you have a big, heavy, slow bike with bad brakes. The new Harleys have the twin cam, fuel injected 88inch engine which is far superior but mega expensive if you can find one.
I have a FXSTC 1987 Harley. I love it, but I have heavily modified it though the years, and I have done time wrenching on bikes for a living. Harley's are hardly bullet proof, especially when compared to japanese bikes. I have one Harley, one Kawasaki, and one Ducati. The Kawasaki is so dependable it is boring. The Harley is pretty dependable, but there are things you have to accept with Harleys, like the push rod tubes leaking oil and stuff like that. If you are going to buy one bike and keep it twenty years the Harley is a good bet. Parts will always be available, there are parts in JC Whitney catalogs now for Harley 1947 knuckleheads. Jap bikes change so often parts may mean a trip to the salvage yard. Harley's are "cool", what ever that is worth to you. The flip side is that they are heavy and slow and can be temperemental. They are also extremely expensive and they are stolen quite often.
If you have the bucks, you can do anything you want. But for $5000 you can buy an excellent low mileage jap bike that will go as fast (or as slow, no rule that you have to go as fast as it will go), have almost zero maitenance, and be as dependable as the sunrise-provided you keep a good battery in it. From a practicality standpoint it is a no brainer, but a motorcycle shouldn't be a rational decision. If you want to cruise, get a cruiser, go fast-get a rocket, tour-get a sport tourer or a full touring bike. One hint: ride what your friends ride. Just because everybody says get a Harley doesn't mean you should. How many of them own them? Almost all of my friends that bought Harley's ended up selling them, most for financial reasons. Some of them still have Harley tatoos, but no bike. Most important thing is getting out there. I have had a bike since I was 8 years old, it is as much a part of me as anything. I don't care what anybody rides as long as they are safe and they are ready to go when I call them on a Saturday morning to go ride.
My $.02