@Kingshead as far as my first bike goes, I'm torn between the 750 Shadow Spirit and the 750 Shadow Aero
Used or new?
This is a pic of the 2011 Aero, no Spirit offered for this year. This bike fits my style choice of a retro bike very well, a very strong contender. The only color option I saw was this winberry red, this might influence my choice.
This is the 2011 RS, if you like the Harley Sportster this is the bike for you. I kinda like the more traditional aggressive stance of a standard bike that it seems to do well.
This is the popular Phantom, many new members here riding this bike. There seems to already be parts for modding and making one your own, you can see some great ones on this site. I really like it's minimalist approach, especially if you help it more in that direction (bobber).
This is the 2009 Spirit, the last year it was offered. Most likely you will be able to find some new ones still unsold at very discounted prices. This is also my last choice of the bikes pictured. Each of the others has a certain niche and fills it well, where the Spirit seems to have lost it's identity. If the austere look of the Phantom isn't to your liking but it's lines are, then this is the bike for you.
If buying a 2009, this would be my choice, again the Aero. Hopefully the 2011 line-up offers this color combo. This bike really meets my requirements for a retro bike.
So, which bike wins as my choice? Well if I was limited to these as my offerings it would have to be the 2009 Aero. First, the cool retro styling. Second, as it's a 2009 and essentially 2yrs old the minute you leave the lot it should be offered at rock bottom prices. Last but not least, I see some great potential here for customization. The Phantom was a very close second but the seat kills the look. Modding would not only be possible, but required. But when modded as seen elsewhere on this site, it's a showstopper.
If not held to these models but still a recent Honda? Then this bike right here, the 1100cc 1999 Aero. The retro styling is off the chart with the beach bars, speedometer mounted in the headlight bucket, and it's stretched out look. This bike would need very little in the way of mods to fit right in with my requirements. Picture this without the fecking windshield and rawhide tassles.