Seriously that all depends on your age. The young guys say the duece is fine and for over 40 years I rode bikes like the Superglides, Low Riders and Night Trains and thought they were fine until at the age of 62 I rode the Heritage and bought a new 2010 Heritage Classic and this will be my last bike. The ride and comfort is a whole world of difference and the six speed transmission is just the ticket for open roads. The difference that the bigger tires make and the floor boards for your feet along with the bigger seat make the long rides less tiring. From the way you describe the type of riding that you do, I would definately recommend the Heritage or Deluxe , whichever you prefer the looks.

 

Pretty much either can go the distance and either is just mostly a look. Deuce will normally need some additions which are fairly expensive except for just hang on bags. Night and day difference in the look. Would guess the Deuce would be a better ride for 85 miles over the Sporty. Stock Heritage seat better then the Deuce. Do not think the weight would matter much. Suspension is pretty much same in back. Not sure about braking. Know tire looks bigger in front but it's still a small foot print on the road. Like you I just like the look. Least it still looks like this 63 old has some rebel gypsy (ha) left in him even if it's just a look. If you really are going to travel get the Heritage. Last bike I had had floorboards and I had to add stirrups to the pegs of the Deuce for comfort and safety at night on the interstate. Miss the hill and toe shiftier.

 

I would agree with everything thats been said this far, except for the comment on age having anything to do with it.
The longest ride i've been on the duece so far is just over 200 miles, mostly local riding of about 50 mi. Although the duece is probably not as comfortable as the heritage, it's still the bike for me.
I would say the biggest difference, is mostly the looks between the two.

 

Thats just funny, but hey whatever gets it done.

To the OP, the 2 bikes have completely different looks, its all on your preference. It also depends on your idea of "comfortable" and thresholds of pain. The heritage you can rent and test ride for a day. They obviously don't make the duece anymore, or even a softail standard. The blackline would probably be as close in ride similarity of a duece that you could rent and try out. Either of them will be an improvment in comfort over your sporty.

 

The Deuce is a cool looking bike but the 2008 Heritage will have the 6 speed along with the 96" engine with no cam chain tensioner worries.

 

The Deuce is a great bike and can do long distance just fine. The biggest problem for the bike is having enough storage (luggage). I put a set of Fat Boy bags and EZ Brackets on mine, and changed the seat to a Corbin Gunfighter dual. I can now spend the whole day in the saddle with no problems.
Here's the bike with a Sundowner seat on it, during a 7 day Nova Scotia tour (2up).\
(I just turned 67)

 

Good comments from all so far. I am taking notes. Both sellers have offered to let me ride the bikes but either the weather has been crap or I have been working. It is good for me to have some idea of what to check out when I do ride. I am hoping that they are both available long enough for me to take those rides and decide. Both are in great shape, well maintained, low miles and no major mods so I can do what I want with either one without buying someone else' changes. As I consider what I am going to do with the bike I can't really see me taking much longer than 200-300 mi ride except couple times a year. With that I lean towards the Deuce. But I truly understand the drawbacks of not having floorboards' storage, bigger engine and 6 speed that are there when you need them with the Heritage. Good stuff! Keep your comments coming as I am going to take them with me when I take those test rides. BTW I am an older guy too but with young at heart attitude.

 

One of the reasons the son sold his, just look in the book, U'll see fits all FX's except a Deuce a lot.

The other reason was his back started hurting after about 2hr of riding.

 

Why would a Deuce rider have to use bungees? Throw over saddle bags and a tour pack on the passenger's backrest gives me a ton of room. What's cool is that after I'm done doing 400+ mile weekend trips, In about five minutes, I can remove all the bags and switch out the touring seat for something more low profile and with the passenger backrest and have it look even more sleek and badass instead of having luggage all over it.

It's great having a bike that can perform double duty, touring and looking good cruising shorter distances.

 

Getting my cylinders bored to 95", head work done, and a cam. Should be pushing over 90hp and close to if not slightly over 100ft/lbs tq on a reliable build without a very high CR.