I've owned an 883 and 1200 Sportster. I bought the 883 because I had never had a Harley and I wanted to try one, but didn't want to spend much. Within months, I had the Harley bug and upgraded to a 1200XL Custom. It was a 2002 model that vibrated a lot and the Custom has shortened suspension that was unbearable on the roads around here. I believe Harley rubber mounted the Sportster motor in 2005, so they don't vibrate like the older models. I think a newer Sportster that was not a Custom with lowered suspension would be a decent bike. The roads are just too rough around here for the shortened suspension. A buddy of mine had a newer 1200 and it was pretty nice.
I went from the Sportsters to a Deuce to two different Road Kings. For longer trips, the Road King is awesome. The Deuce was nice, but it had forward controls which I don't like for longer rides. With your feet forward, all of your weight ends up on your tailbone. The Road King has floorboards. When I got my first Harley, there was no way that I would have floorboards or a windshield. Now, I wouldn't do without either one of them.
If you think you might like to go on longer rides, I highly recommend the Road King, but it's a bigger bike and maybe not the best to learn on. It would also be better for passengers, but I wouldn't recommend having passengers until you're really comfortable with riding.
If you buy a used Sportster at a good price, I don't think you would get hurt much on dollars if you sell it later to get a bigger bike.
I went from the Sportsters to a Deuce to two different Road Kings. For longer trips, the Road King is awesome. The Deuce was nice, but it had forward controls which I don't like for longer rides. With your feet forward, all of your weight ends up on your tailbone. The Road King has floorboards. When I got my first Harley, there was no way that I would have floorboards or a windshield. Now, I wouldn't do without either one of them.
If you think you might like to go on longer rides, I highly recommend the Road King, but it's a bigger bike and maybe not the best to learn on. It would also be better for passengers, but I wouldn't recommend having passengers until you're really comfortable with riding.
If you buy a used Sportster at a good price, I don't think you would get hurt much on dollars if you sell it later to get a bigger bike.