I own a 2004 883 Sportster with several performance mods. When I decided it was a bit cramped riding with my wife, I tried trading it in and getting a bigger Harley - but even the Harley dealer didn't seem to want it. Then I found out that Triumph was back in business. I always had a soft spot for Triumphs. I bought a Speedmaster (which is dimensionally about the same as a Softail) for far less than it would have cost me to trade the Sporty in. I now own both a Sporty and the Triumph. The Speedmaster is far quicker, handles far better, is far smoother, etc. Yeh, there's a part of me that still likes the Harley, but bike for bike, there's no comparison. Don't risk your bike - it ain't worth it. If you want to blow him away, have him stradle his bike and just tip it up off the stand, then have him stradle your bike and do the same - it's that top heaviness H-Ds drivers are fighting all the time they're riding.
