I'm buying used. Right now in this area, a local dealer is trying to dump inventory which hasn't moved over the last couple years while the economy dropped. People are buying brand new half price bikes, which is making people looking to sell used bikes more willing to drop thier prices. I'm getting my America for less than I believe it is worth. It makes it easier to swallow any other money it will need. I know mine will need its 12k service, but it is still not exceeding it's worth.
I have chosen the America because of how it sits for me. I like to ride with my arms in a certain position, but I'm thinking of getting the risers like the speedmaster has to bring the bars up and back that one more inch which is perfect for me. I also like the chrome of the America.
I also struggled between Speedmaster or America. When I ride my husband's Speedmaster it is perfect, except for the bars.
As far as the chain, and such, if you get a good price, a fix is easier to take. Husband's bike ran great even with the chain real loose until we had it adjusted. These bikes are great! I look forward to tinkering with mine.
Do you have a shop that you trust? Before final sale, you can have the bike inspected to know what you are dealing with.
Just get one and I'm sure you will be very happy.