I'm approaching my 59th birthday and started riding at 8 years. I've owned some 25 motorcycles in that time and a few scooters. I've owned two Sportsters. First was a new 1984 XLX1000. Second was a used 2006 XL883. I liked them both just fine. The 2006 was about the perfect bike for me, especially since my wife doesn't ride on the back any more. Be aware that the Iron has lowered suspension for that slammed look. My Sportsters both had standard length suspension. The Iron won't have as good of cornering clearance. I worked at Destination Harley-Davidson in Tacoma, Wa. for 5 years. A coworker that had a Nightster (with the shortened suspension also) followed me to work one morning on my XL883. It was a great winding country road along farms and a river. He couldn't believe the lean angles I got (me being an old geezer too). He couldn't make the corners like I could due to scraping hard parts. HD goes to shorter shocks in the rear and shorter fork tubes up front.
I also bought a new 2007 Royal Enfield 500 Bullet Classic in the British racing green. Great looking bike and mine did quite well. If you want to be noticed, buy the Enfield. I have never had so many strangers approach me asking about that bike. They handle well, are way lighter than any competition, look great, get great gas mileage, etc. The valves were the easiest to adjust I have ever seen. With the tool (a wrench) in hand and the bike at TDC on compression stroke, I could check the clearance in maybe 30 seconds. Adjusting took another wrench and maybe 5 minutes tops. Oil and filter changes were more involved than most bikes, but still no big deal. Mine used no measurable oil between changes. As in I never had to add any.
I also rode genuine old timey Britbikes back in the 70s. And I've owned a bunch of dual sport bikes.
When Triumph (Hinkley Triumph) came out with the Bonneville I rode my Kawasaki 500 Ninja to a dealer and took a test ride. I liked it a lot, and love the looks too. Haven't bought one yet. Life is just too dam short. Right now I want to get another dual sport.
Best of luck in your choice. Test ride that Iron. At least HD dealers still do test rides.
Jon in Keaau, Hi. USA
2008 SYM HD200 (wife's ride)
2009 Kymco People 150 and coming soon, another dual sport mc