Hello

My money would be on the 2011. The issue with the headlight wiring has been largely dealt with by 2011 but i think its always best to upgrade to whats called the Eastern Beaver relay kit out of japan. OR go one better and put a @DEcosse Keyless Ignition in whatever rocket you buy - no fumbling with keys as it stays in your pocket and the system provides all the power to the headlights with no issues.
 
... The issue with the headlight wiring has been largely dealt with by 2011 ...

2011 Roadster Models do not pass headlight current through the key-switch
Even 2010 Roadsters, although leaving factory with similar scheme to the Classics/STDs, SHOULD have a recall retrofit installed to bring them to same std as 2011.
Not that a KeyLess Ignition is not a fun add-on regardless
 
Welcome Shane, from Maine. It's a tough choice, but any Rocket will do and then some. Personally I'd go newer, seems properly set up for your wife too. Sorry to here about her condition and wish you both the best, a Rocket WILL bring many happy times I'm sure. Just do it and start riding, you'll feel a great relief once the decision is make and you'll great anticipation of your first ride. You should test drive each before purchase. I 05 may need new tires, I'd have them changed out if you go that way.

Hoopla
 

OK Knight this is the bottom line... ABS. It has ABS ! The arm rests are nice. They will offer much security to your mate and stability for you. The 11 it is. Squeeze the guy down. I'm sure nobody other than you has even come to look at the beast.
 
I'm sure either one would have been really good but given my wife situation I decided to go with the 11 with everything that has
 
It's a great feeling isn't it, Congrats! Wishing you many miles of smiles. Had mine out this afternoon, still smiling.

Hoopla