I understand how difficult the decision could be to purchase a
starter bike. I googled the 2009 iron 883 and saw the MSRP of around $8000.00. Figure another what, $1000.00 to get it the way you want, plus tax and tags, that's a
lot of scratch there for a starter bike.
If we were not talking
starter, the Suzuki S83
http://www.powersportstv.com/models/Suzuki-Boulevard/2008-Suzuki-Boulevard-S8... has so much more bang for the buck, and you would leave those Sporty's in the dust on the highway for around the same price as the Iron. But it's a lot of bike to handle for a newbie, and we are talking starter bike. The Suzuki S50 is another slamming bike for a lot less money than the Iron.
I'm sure that you want something reliable also, so you may not want to buy a very early year Savage unless you're good at wrenching. You could find a later model S40 for under $3000.00 if you're patient, should you decide to go that way. I paid $1000.00 for my 87 with custom paint and a SuperTrapp. One of the best motor vehicle purchases I've ever made. I love this bike.
I'm 5' 10" and I'll admit that my knees start hurting after a couple of hours of highway riding on the Savage, but I've not yet installed forward controls. The seat gets you also, but there's a simple inexpensive mod for that. Really, every mod on this bike seems inexpensive compared to HD's.
I've owned 2 Sportster's, both Iron Heads. My '72 was a great bike and I'll always regret getting rid of it. My early '84 blew a rod. That bike gave me a lot of headaches for some reason.
If it were me, the Iron 883 would not even be on my list at 10 grand, or 9, or 8 for that matter. It may be affordable to some, but for that kind of money, I'd rather go for an earlier year sporty if I must have an HD, or find a Savage for under 3, actually $2000.00 would be good and can be done, mod it and use the cash I saved travel around Central America for a few months during the winter.
I wouldn't worry about keeping up with anyone else's bike. If they're gone, they're gone. I'll meet up with them later. I like riding solo most of the time anyway.