Anyone that does a minimal amount of research can't avoid the numbers or the fact that the 106 is a superior engine versus the 103. That said you don't ride an engine. The engine is one element (an important one) in the total scheme of things involved in making a decision about buying a particular motorcycle. Some of those issues are based in emotion and with some individuals it's 90% emotion. When I was 21 years old I made a lot of decisions based on emotion. If facing the same decision at 21 years old (Gunner, Highball or Street Bob), with very high emotions wanting my first Victory, I would have probably thrown rational thinking and any sense of financial responsibility out the window a went ahead with the deal on the Gunner or Highball. But 21 is a far distant, four kids, fifteen grandkids and two great grandkids (one in the oven), memory and the rational side of me couldn't get past the trade-in issues.
I don't know about the history of trade values on HD's versus Vics. I got a good deal on the trade-in and the new bike from the Harley dealer. I'm not sure if the same deal could be made this year given what I've read about the huge inventory of used motorcycles they have on hand. At some point the cost of having that inventory is going to hurt and hurt bad, especially if the economy continues on the track it's been on since the start of this year. O.k., I ramble on...
With respect to many if not most buyers, most are going to get a bike with a stock engine and at the most go stage 1. Price wise the 106 bikes are typically going to be the better deal but you're still going to have buyers that are going to pay the extra to get the 110, with all the "stuff" that comes with buying a Harley (importance of which is a personal matter), over the 106.
I think the guys that have the know how, desire and dollars to do major upgrades, and understand the potential of the 106 versus the 110, may go for the 106 because in the end, after all the modifications that can be done are done, the 106 is going to sport the better numbers and performance they are looking for. I leave that stuff for HC and the other guys that really know what they're talking about to discuss while I sit on the sidelines, listen and learn.
One last comment, so there is no misunderstanding (not by you or most) let me reiteration a point for the internet psychoanalysis on the forum, I like Victory motorcycles but nothing in what I've written should be interpreted by those internet psychoanalysis as I don't like Harley's or I'm not happy with my Street Bob or that I really, really, deep down inside my subconscious mind, begrudge the fact that I had to "settle" for a Street Bob.