A friend of mine told me that you can get extensions to forward controls. I'm only 5'8" tall, but long trips kill my legs on my nightster, so i'm going to look into the extensions. I think they have 1-3" extensions, i have to talk to him again to find out the details or maybe the shop my bike is sitting at right now.

 

I had been thinking about that too.
There's a guy on these forums that made them in the past.

Can't find the post, but it rings a bell.

 

You can do awesome things to a sporty. I remember a thread about sportsters from France, they looked amazing. The only thing that wont work, IMHO, is to make a comfortable touring, good looking bike out of it. You want comfort? Sacrifice looks. A big seat on the narrow sporty frame looks odd.
+1 on the detach stuff, atleast, you wouldn't have to have the awkward look while riding around town.

 

#1. change out the suspension. Put a set of Progressive springs in the front forks and change out to a heavier fork oil. Go to a set of Progressives in the back or a set of air shocks off an RK or street glide. You'll find information on this in the Sportster section.

#2. Get the quick detach windscreen and and other quick detach options you want. Mine (see photo below) has the quick detach windscreen, the Easy Bracket system for the saddle bags, and the quick detach backrest / luggage rack.

#3. Upgrade to a decent aftermarket seat with sufficient padding.

#4. Adjust/exchange your bars for your comfort.

 

My theory is that nothing you do to a Sportster will keep it from looking better than anything else Harley makes. You can put a potato sack on a super model, but she will just look more like a new fashion statement. My Sportster needs only one thing to start on a long ride--turn on the switch.

Go for comfort if you are putting time in the saddle. No future in discomfort.

 

i have an 08 nightster with 35,000 miles. i've changed the rear shocks and added the passenger peg kit. i routinely ride 1200 miles per weekend. just telling you this so you'll understand that i'm not floating a couch down to bike-night and then telling you what works and what doesn't. i'm talking from experience.

if you're going to look at another bike, look at the triumph sprint ST, the buell uly, the kaw concours, used goldwings, etc etc etc. one of the biggest mistakes new riders make is chosing a bike based on looks. now that you've experience, you should be able to chose a bike that suits your needs.

you can shop a brand, but you'll just end up with the wrong bike again.

there are some things you can do to improve your bike, and they aren't necessarily expensive. the first thing you need is more suspension travel. you can keep your trees and lowers, but the fork tubes, springs, and damper tubes need to be replaced with those from another model (and R would probably be a good choice). you can lower the bike in the trees, if necessary.

Rear shocks can also be had for cheap. If you hunt the interweb for the term "whittlebeast hybrids" you'll find information that explains how to put your lowered springs onto a longer shock body. again, if you simply must have a certain look, you can get lowering tabs for the new shocks.

once you have more travel, you'll want to ensure you have the right spring-rates. if you weigh 300 lbs you need springs that are sized for you. also account for luggage when sizing spring-rates.

the seat may not be as bad as you think. seating position if everything, and with longer suspension you may find the controls easier to deal with. but i gotta tell you, forward controls are uncomfortable for long rides unless you have lots of wind-stoppers and a very thick/wide saddle.

if i had it to do all over, i'd go check out the buell uly first, because you can get it with hard bags, heated grips, and a wind-screen, for a good price. it gets rave reviews and its owners claim to ride 16-hour days.

if you stick with the iron, don't be afraid of raising it with longer suspension. mine is raised about 4 inches and still gets plenty of compliments. the peanut tank and bobbed fender is a good combo no matter how low the bike sits.

 

I'm sticking with the Iron.
The way I see it is 5 days out of the week I will only be riding around town.

It's not worth getting a huge, comfortable, and expensive bike for a minority of my riding time.
I'm going to use the detachable addons for comfort/storage when I need them and go bare bones for around town.
I have no problem around town, it's only after 30+ minutes of continuous riding.

On the way down to FL I did a 14 hour run. It was not pleasant.
I don't plan to do anything big like that for a while, just longer rides on the weekend.

Thanks everyone for your feedback, I have a plan of attack.
Windshield, Seat, then shocks if I need them.

While it probably won't be a good as one of the bigger bikes, it should be noticeably better.

 

They make an air ride kit for the sporty, that'll get you adjustable ride height, and an improved ride, gel seat with back rest, windshield, 1200 kit, 6speed, ISO grips / pegs.
Do all this and your bike will be ALMOST as comfortable as a Dyna. Forget ever trying to be as comfortable as a touring bike. If you ride enough you'll get tough and wont need to make any mods at all.

 

LOL I wish I could place I bets that you will get a Fl. Your having second thoughts now....It's just a matter of time.

 

Windshield $124

Windshield Hardware $98

Wide solo seat with backrest $413

(probably will fit your Iron but should be double-checked with Mustang)

Progressive rear shocks $220

(again, will probably fit your Iron but should be double-checked with Drag Specialties)

Subtotal before shipping and taxes = $855