You obviously want the savage. Thats why you posted on here. The savage is fun to mod and addictive too. You have a simple bike to start with, a canvas, and you beautify it however you want it. The savage club is a wonderful and supportive club. At 155lbs wet, this bike is a rocket for your light weight.

Are you talking about the V-Star 650 custom?  It looks cool.  I rode one for a total of about 6 hours over three different days.  I was so glad to get back on my S40 though.  Much more grin factor with the S40 all around.  The V-Star 650 is a bored out and bloated Yamaha Virago 535.  Now the 535 is an awesome bike.  It's like the S40 in size and weight, but you got another 10hp and v-twin torque.  The 650 version, IMO, is like a 4-door family sedan with a 4 cylinder motor.  It doesn't accelerate but simply gathers speed.  If you like a bike to do something when you turn the throttle, you'll get bored with the 650. The 883 is sweet.  Most people do mods to their bike, even when they initially say they won't.  It'll cost you twice as much to do the same mods on a 883 as you'd do to a S40.  The 883 has a good bit more power but also a good bit more weight.  I do a lot of downtown, stop light to stop light riding.  So the extra power in those situations does little for me.  But the extra weight of the 883 in those riding circumstances would make it less fun for me.  The engine would handle riding two up better that the S40 or the V-Star.  The V-Star, however, would provide more comfort for a passenger than the other two but lacks the power to enjoy it IMO.  Since you pointed out the $$$ of the 883, I think a late model used S40 would be the best bet for you.  It is user friendly, both riding and working on.  

By most accounts if you are over 5' 8" you will be slightly cramped on the S40. You can modify it, but that adds cost. You could also consider a different genre of bike. The Kawasaki 250 Ninja costs about a grand less, and will outrun a stock S40, although published reports give the S40 a little better 0-60 time. My 2007 S40 has averaged about 55 mpg for over 5000 miles, with a low of 39 mpg running 75 mph into a headwind and a high of about 73 mpg riding in the Rocky Mountain Park with 35 and 45 mph speed limits. I don't have as much data on my 2007 250 Ninja, but it seems to be averaging about 67 mpg over nearly 3000 miles. Only you can decide on the balance of looks, performance, comfort, cost, and so on that you might want in a motorcycle.

Ridden them all. Savage kills them in the grins per dollar ratio. Buy one used, the ratio goes way up. I did not hesitate to modify, perform maintenance, or just plain make my own because the initial investment was so low.

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.

I read here some time back that a stock 883 and stock savage are pretty darn close in the 0-60. I think teh savage is 2/10ths of a second slower. I PROMISE you wont lose your buddies while riding unless they're doing 90+ for extended periods of time. If they throttle up to try to lose you for a minute or two throttle up and you'll stick right with them. My best friend got a '95 with something like 7k mi early this season for $800. Came with a windshield and Jardine exhaust. Try getting a better deal with a sporty or vstar. I like sportys personally but I also like my cheap...everything. For the price you really cant beat a savage. You can take all those extra thousands of dollars that you wouldve spent on a stock sportster and modify a savage/s40 and blow just about any bike out of the water 0-60. DIY performance intake, performance muffler, performance cam, chain conversion, cast wheel conversion, seat mods, lighting mods, forward controls...all available here for little cost. Ive never heard any gleaming reports about the vstar. Its okay...not great from what I hear. And it looks too "american" for me. It looks an obese dog IMO. Obviously Id go with a savage/s40. Its small enough physically for a beginner to control without issue (only 40lbs heavier than most 250s) and powerful enough to get you into or out of trouble (I hit 80-85 just about everyday on my way to work. Speed limit is 55). Cheap to insure ($88 a year, full converage), cheap to buy (see above), cheap and easy to maintain (if for no other reason than you've only got one of everything rather than two), its unique, its been basically unchanged for 20 years. Its highly unlikely you'll ever find the PERFECT bike for you off the floor, but considering you're probably going to make changes anyway (ask the HD dealer how much to put forward controls on that sporty you're looking at. $95 for the savage) you might aswell save some serious cash and make them to the savage. Plus...being a new rider, how would you feel if you laid down your expensive new sporter or v-star? How much would it cost to replace a dented tank? +/- $50 on ebay for the savage. I'll make you a bet. Buy a savage now and keep the rest of the cash you wouldve spent on something else. Ride it for the season. If you honestly regret the purchase sell it and I'll send you $100 to go toward whatever bike you intend on replacing it with. If you DONT regret it you owe me a 5th of Sailor Jerrys. Deal?

First bike, Go low weight, low price & used.

This is the first bike Ive ridden over 10,000 miles w/o crashing. Ive dropped it in the yard on sloping wet grass, but never straight up Crashed.