WT,
Congrats on returning back to riding. I only have a few thoughts to offer. First, right now there appear to be a lot of good deals out there due to the economy, so now appears to be a good time to buy. Secondly, how tall are you and do you expect to ever have a passenger ride with you? If you are a taller or larger man, or if you might ever have a passenger, the 883 is less than ideal in terms of being comfortable for you and even possible for a passenger. Third, the 883 has a bit higher center of gravity than some other options on the market (a small issue and usually only for newer riders). Aside from that the Sportster is a great bike. I do agree with others regarding 1200 vs 883. If you get a Sportster get the 1200 if possible. As an option check out used bikes for sale. There are thousands of super low mileage bikes out there that were bought for recreation, have barely been ridden, and are being sold due to economic conditions. I would recommend looking at the Honda VTX 1300 as an option. SOme dealers have been advertising great deals on the VTX to get old stock out of their stores.