There is a good used market for the bikes at present. My youngest brother just bought his first one a couple months ago. His is the black one in the back, it's an 06 with about 20K on the clock. He gave $3K for it.
My other brother owns the red one in the front, its a 96 in very good shape, low miles. He bought it about two years ago for about $2800.
Mine is the middle one, its a 1995 I bought new.
They are all 883's, we all ride two up at one time or another. I just went back to the single seat and lowered rear end this year. But my wife and I have ridden hundreds of miles two up and I have ridden thousands of miles on it. I'm 6 one and not frail...
My baby brother is six four and he was riding his girlfriend the day this picture was taken. The picture is a couple hours from our homes.
Find the best deal you can on the newest bike with the lowest mileage, but I would not let 883 vs 1200 play too much into it. You might read up on rubber mount and EFI and when those changes where made. Some folks like the change and some don't.
Of course 1995 was the best year they made them and the last year for the peanut tank.
But don't ask my brothers, they seem to have different ideas...
(All three bikes have had some minor jet work and exhaust mods done.)