Ultimately it's up to you and what you want, personally I'm not going to pay 10k more for a bigger bike with identical or marginally better performance that is heavier and harder to lug around. Not to mention upgrades typically reflect the cost of the bike and the bigger/more expensive they are, so are the upgrades.

That being said, I'm 6foot and weigh 260lb and rock a forty eight no problem. I bought the bike when I was 220 and over the past couple years gained 40 lbs, so the bike does feel a little slower but that's just more motivation to drop the cheeseburger and get back down in weight. Think of it as a free performance mod, personal weight reduction! Even still I hardly noticed the change in performance.

I have some mini apes and that made a world of difference, without them the bike does look kinda small but it is still rideable. My brother is 6'6" and bought an 883custom as his first bike, he was worried about size too but with forwards and the way the bars were set up on that bike, tied with the big skinny front tire and it was fine for him.

If you're still unsure I recommend going to the Harley website and using their compare bikes feature. I think it's funny how all of these guys tell you you NEED a bigger bike and youll want to upgrade but I feel as if they just fed into the harley hype and were more concerned with being picked on for their bike than enjoying the ride. If you look at the forty eight against their lineup you'll find that most of their bikes have about the same seat height, and only have about a 5" longer wheelbase so the whole bigger bike arguement is kind of a sham.

Don't get me wrong I'm not trying to downtalk anyone, there certainly are better bikes for longer trips and whatnot but if you're looking for something that's just plain fun the sporty is a good choice. A sixth gear would be nice but then again I don't go much over 65mph so for someone like me its fine, also I wouldn't recommend going much faster than that without a fairing because getting beat up by the wind gets old pretty quick and since the sporty is light if it's windy it can be a pain to keep straight. Just my worthless opinion but hope this helps! Enjoy the ride

 

Really good info here. I own a 2007 Softail I rode for a couple of years back in Texas. It is currently in storage there as I have moved to the Philippines. I looked here for a bike to ride as well. Looked hard at the softail line and others and came to the same conclusion as TheFallen. There was just not enough difference to justify the nearly doubling of cost. It was amplified here in the Philippines as the Harleys here are double or more than they cost in the states.... So the cost issue really jumped out at me. They wanted about the same money for a good Softail as I paid for a 4X4 top line Wildtrax Ford pickup!!!

So, I put my money on a Sportster Superlow. And then made it my own. I am 5' 11" by the way. It seemed small to me. BUT..... I put forwards on it. And I put a really good two up seat. I need to get the shocks changed out to taller shocks as it is too low to cleanly ride here with the speed bumps around here. It bottoms out on the bumps and knocked all the paint off the bottom of the bike already.

My softail is quite a handful as it is heavy. But it can eat up the road like nothing I have ever ridden.

Pic...


The Softail

and the Sportster as it came from the showroom.....




And now, ready to ride with help of a ferry, to the next Island for a tour with the wife...............




Just make it as your own. As TheFallen says, only 5" difference in the two bikes. I actually did not know that!! You should think through it...

 

6’3” 250lbs. 3.5” Accutronix extended forwards, Mustang seat to push my butt back 1.5”, 16” bars on 3.5” risers. Who says Sportsters are for small people!

 

I’m 5’8” and 150 lbs but I did same as you-Mustang seat with backrest and Accutronix extended 6 in farther forward, and rox risers for up and back and now its awesome for long trips
i also got better and taller shocks from DK Customs which are better but still kidney busters on bumps
going for better suspension soon
i never plan to ride my softail anymore
sportster is more reliable