Quick background....
57 yo male... been riding since I was 10, have has at least 200 motorcycles, most dirt, I'd say 50 or so street bikes, all Japanese.
1980 - 1983 I worked in a small Harley dealer, rode new Harleys all the time, dealer bikes.
2009, wife talked me into getting a Harley, bought a used Softail, was OK, she LOVED that bike.
She talked me into getting an Ultra, bets thing I ever did, we have FUN on that thing. --- I always knew women LOVE Harleys, all good.
I sold and replaced a Kawasaki 750 -2006, bought a used 01 Sportster for my "around town" bike.
That Sportster shakes and vibrates like crazy but its so damn fun.
Harleys are what they are, so many bikes might be better but they are not Harleys.
Many threads on here about how a guy is disappointed with his Sportster, either enjoy it or sell it, they sell quick.

 

I am 56 and my 2017 Sportster is my first and only Harley. No regrets. Having a blast. I do have a lot to learn though.

 

I am on my 3rd Sportster. My first was a 1975 XLCH. Had her for 2 weeks, tuned her up, put on new tires and rode to Rhode Island with my wife. Sold her for a 1994 1200 Sportster. That one went to Laconia a couple of times. Had a 2004 Triumph Bonneville that I went down on in 2006. Great bike. Didn't ride for 11 years. This past January I bought my 2007 Sportster Low. I've put about 3000 miles on her and love the bike! Oh, and I'm also 56!

 

I'd agree.
Good bike or sell it.

Pros: great around town, can "do it all" bike, good commuter/lane share bike.

Cons: lack of fuel range, not so great two up, big twin envy jokes.

 

I've had several bikes that I've replaced over the years, and the only one I regret selling is my Sportser. I loved that bike, and wish I had kept it. If I had room for another bike, it would be a Sportster Iron. It would make a great "around town" bike.

 

Love mine to death. Did have a weak moment recenty and consider trading it in on a 2018 fat bob... lasted a full 3 minutes. Nope. Mine!

 

Mine is not going anywhere. I might add to the stable but this is the funniest bike I e ever had.

 

My only regret with Sportster is not having one right now.

 

My first Sportster was a 1973 XLCH, then Dynas, Touring, and a Softail. I have wanted a 1200R for quite a few years now and last year I picked up a 2006 1200R. I love it to death.

 

Not sure if you could call it "regret" because I still miss my 04 Roadster.
But hindsight being 20/20.....despite that it was great fun, especially on the back roads....it was just the wrong bike for me to start with.

I spent a lot of cash trying to make it more comfortable....seat, forwards, suspension upgrades ect. ......but it was no use. I'm a big guy and need a bigger bike.

I should have started with a Dyna, which is what I eventually traded it in on.

Dyna is just a much more comfortable platform for a full sized guy.
(but even then I traded it on a Road King, which I suppose was kinda my long term goal all along ).

So...regrets? Yeah, I regret I couldn't afford to keep all three bikes.