I am a fat old man, 62, 6' and 250lbs riding a beautiful excellent running 2002 Dyna wide glide. I love the way it handles and leaning in curves on the throttle at 35% is a hoot. Fellow riders say its a woman's bike that I need a bigger bike for my size. They all traded up some to Heritages and the big baggers. My problem is the 88cu with 15,000 miles just cant keep up with the big boys on the 400 mile rides. A full upgrade to 95", all the good stuff to 95+hp/tr is $4500. Even this still puts me way behind the 103"s, with their bigger tires, fuel injection and all the other improvements in the newer bikes. A new Heritage cost $19,000, bagger at $24M. So my question is, does it make even remote sense to upgrade the old 88's at this point? Seems to me old bikes, even spending $10M less, is just not worth the investment anymore. Any good advice from experienced riders.

 

What is keeping you from staying with the "big boys on the 400 mile rides"? Is it comfort or speed? If it is comfort upgrading the engine won't improve comfort a lot.

 

Yeah, my 97" build will smoke a stock 103 bagger no problem. I also do distance, but I can't say it is the most comfortable after 3 or 4 hours straight.

 

I would go with a newer or new bike.

 

95hp will put you way above a stock 103, especially in a bagger. I've never heard anybody call a Wide Glide a woman's bike. And you said yourself you love the bike. So why trade? Spend a couple bucks on it if you want to, upgrade the cams and tensioners, and be happy with it.

 

Also, your bike has the last year of the sturdy forged crankshaft. Build that bad-boy up, and $4500 is steep. You can get well over 100/100 for much less.

95ci - 98ci bore
S&S 570 EZ Start cams
Big Boyz head work
Mikuni or S&S Carb
Maybe a new Ignition
adj Pushrods

 

Keep it, cam it, pipe it, tune it, and blow your buddys away !!!!!!!!

 

Upgrade your bike or get a new one. I'd what you need to do and what your finances will let you. Or ride solo.

 

If I like a bike, I'll always put money in it before I go looking for something new. I've had a number of bikes that I have "loved" (those are the ones that you always want back). I've also owned a number of bike that were good motorcycles and suited a purpose, but something was missing about how I viewed them (I've never once wished I had one of them back after they were gone). Sometimes it has to do with the work you have done to the bike, what trips you've taken on it, how long you've owned it, ect. But at least for me, when I put money into a bike I really enjoy, it always makes the ride even more enjoyable. I don't know your financial situation, but I would also say that a bike is always more enjoyable to me when it is paid off. I would always put money I could afford into a good bike that I own free and clear before I financed anything.

 

If you bought the Dyna new in '02 you are only riding 1500 miles a year. You need to ride more to justify a new 20k bike. To add to my Street Bob I found an '07 RK that was already a 103. It doesn't handle like the Dyna but it sure rides and goes good. I got the RK for way less than a new one.
See if you can get some riding time on some of your friends newer none Dyna bikes too see what you really want before you decide to "upgrade."