When you click on links to various merchants on this site and make a purchase, this can result in this site earning a commission. Affiliate programs and affiliations include, but are not limited to, the eBay Partner Network.
New to the forum. I’ve decided to get back into riding after about a 10 year hiatus. I rode metric cruisers before and have decided this time around to go with an H-D.
There is a ‘99 Fatboy listed for sale at $5,000 about 3 hours away from me. Normally I wouldn’t even consider this due to the drive and the overwhelming availability of newer twin cams in my area at the same listing price.
The add states he purchased it from a friend a year ago that became ill and had the Harley dealer “repair or replace anything needed”. Named new tires, battery, all fluids, carb service/tune. From the looks of the shop/garage, this guy isn’t likely a motorcycle guy. It comes with a second set of tins that have been custom painted plus windshield, bags and sissy bar with luggage rack.
I know I can probably haggle the price down a little bit as the last Evo Fatboy I saw sell on Marketplace went at a listing of $3,450. Although that seller was very aggressive with price drops and I think he really needed the money. Twin cams have been sitting for months in my area listed for $4,500-$5,000.
I am a gearhead that likes to do his own wrenching but really don’t want to get into something that needs constant tinkering. That’s one of the reasons I’m drawn to this one as the Evos are considered pretty darn reliable and the recent service work done. Plus, just the athletics of the bike has me hooked.
Is this a bike I should consider passing on or go ahead and snag it up?
There is nothing wrong with a well maintained EVO Harley..... But keep in mind, even the best EVO out there is at least a 36 year old bike.
There is nothing about a '99 EVO that would automatically exclude it from my consideration, if looking for a bike in that time frame and price.
I generally advise shoppers, when comparing similar bikes where everything seems to be equal (mileage, condition, appeal, price) to buy the newest bike within their budget, as it will most often have the newest upgrades. But mileage and condition will always count more than age, IMHO.
The pics look good, but you will still ned to do a good inspection. The proof is in how easily it starts, runs, and how the engine sounds... be critical of any noises from the engine, primary, and/or transmission. Check that all electronics (lights, signals, etc) are in good working condition. Look at the areas where most people don't look for red flags like fluid leaks, rusted out hardware, etc.
If while doing tour inspection, you see a red flag, don't automatically accept the sellers explanation... Remember, they are trying to sell the bike...
Always base your buying decisions on what your head is telling you, not what your heart wants... Never be afraid to walk away, if something just doesn't seem right.
Good luck with your inspection and buying decision.
Last edited by hattitude; Aug 17, 2025 at 12:21 PM.
Thanks for the tips!
This bike has 26,000 miles on it. Not “high” or “low”
26K miles on a 1999 motorcycle averages out to 1000 miles a year. That more than likely means periods of use, and periods of just being parked. That type of duty cycle can lead to overdue, and maybe even neglected, maintenance schedules over its lifetime..
Hattitude gives good advice. Do a detailed inspection. If the Bikes in good running condition constant tinkering probably won't be necessary but you will be tinkering. EVO's aren't without issues. Lifters and inner cam bearing is what comes to mind. Overall a good engine and with proper care can last decades if not a lifetime. The bike looks decked out with loads of extras. The extra tins, if in good shape, could be sold to recoup cash paid for the bike. A good wash will get it looking sweet.
One thing I did notice it looks like an oil drip on the exhaust just below the air cleaner. Might be puking a little oil. Overall Harley's are easy bikes to work on. Get yourself a factory service guide for whatever Harley you decide on.
Good luck with your search.
Hattitude gives good advice. Do a detailed inspection. If the Bikes in good running condition constant tinkering probably won't be necessary but you will be tinkering. EVO's aren't without issues. Lifters and inner cam bearing is what comes to mind. Overall a good engine and with proper care can last decades if not a lifetime. The bike looks decked out with loads of extras. The extra tins, if in good shape, could be sold to recoup cash paid for the bike. A good wash will get it looking sweet.
One thing I did notice it looks like an oil drip on the exhaust just below the air cleaner. Might be puking a little oil. Overall Harley's are easy bikes to work on. Get yourself a factory service guide for whatever Harley you decide on.
Good luck with your search.
Good eye on that drip. Looks like it might be the typical breather puke. I can also see some staining on the lifter box. If I do go check it out I’ll be sure to watch for that.
I haven’t contacted the guy yet as I’m traveling for work and won’t be able to burn a whole day to get a bike till after Labor Day.
The picture is a bit out of focus..
But that bike looks like it has been parked and not looked at for years.
It happens....
Confirm tire age stamp.
There appears to be some additional lights on rear and you have to be ready to address electrical if not done right...not a big deal.
The Timer cone cover looks different...why?...looks unusual.
How old are those tires? and there is a lot of balance weights on that rear tire.
Looks like a passenger foot peg on the left but did not observe one on the right? are pipes blocking the possible installation of peg.
The seat looks dried out, weathered or is it just dirty.
What is going on with that brake master cylinder..Throttle side...picture does not look clear in that area...
Are you sure those custom painted parts are for that year?
Appears to have a stage II... basically an air cleaner and slip-ons based on loop behind / above air cleaner.
Overall no major detractors and it looks like someone purchased a lot of chrome parts but with any used bike just be prepared to spend $1000-$1,500 in parts to address items as a "do it yourselfer" with free labor.
Rocker cover gaskets, fork seals, rear shocks, change of all fluids and replacement of a few parts will easily get you to that $1,000-$1,500 parts number.
From a distance it looks like a nice bike for the right buyer.
Do not forget to get key for the lock on front downtube.
The picture is a bit out of focus..
But that bike looks like it has been parked and not looked at for years.
It happens....
Confirm tire age stamp.
There appears to be some additional lights on rear and you have to be ready to address electrical if not done right...not a big deal.
The Timer cone cover looks different...why?...looks unusual.
How old are those tires? and there is a lot of balance weights on that rear tire.
Looks like a passenger foot peg on the left but did not observe one on the right? are pipes blocking the possible installation of peg.
The seat looks dried out, weathered or is it just dirty.
What is going on with that brake master cylinder..Throttle side...picture does not look clear in that area...
Are you sure those custom painted parts are for that year?
Appears to have a stage II... basically an air cleaner and slip-ons based on loop behind / above air cleaner.
Overall no major detractors and it looks like someone purchased a lot of chrome parts but with any used bike just be prepared to spend $1000-$1,500 in parts to address items as a "do it yourselfer" with free labor.
Rocker cover gaskets, fork seals, rear shocks, change of all fluids and replacement of a few parts will easily get you to that $1,000-$1,500 parts number.
From a distance it looks like a nice bike for the right buyer.
Do not forget to get key for the lock on front downtube.
Thanks!
Seller claims the tires are fresh as of last year from Harley shop so I would expect to see a late '23 to mid '24 stamp. If not, that's definitely going to be an issue. They aren't the original wheels and I know aftermarket wheels (at least in the car world) are a crapshoot when it comes to getting balanced. I'm already planning to source some factory solid wheels and will use that in my negotiation. I personally think it's almost sacrilegious for a fatboy to not have the solid wheels.
The timing cover looks to me like it's catching a reflection. I'll inquire if it turns out to not me factory.
The seat is a good point, It does look dirty in the other photo that I didn't post but doesn't look beat up. If it's a little dry, some conditioner might get the job done. No idea if I will even find that seat comfortable.
I did see the extra lighting below the swing arms in the back.
There is a peg there, the photo makes it hard to see.
As far as the extra tins, I have no idea without looking at them. Honestly, I wouldn't run them anyway, I prefer the factory tins. But it would be nice to know what they fit so I can possibly sell them. Likely not for much.
Really appreciate the extra set of eyes on photos!
I reached out to the seller and it sound like he got the short end of the stick trying to help a friend out. Paid $4,500 for the bike and shipped it home then sunk another $3,500 into it.
Work done at the Harley dealer with documentation includes:
Battery replaced
Tires replaced
Fuel system flush and lines/petcock replaced
Carb rebuild
Handful of leaky gaskets replaced
Spark plugs
Brake flush
3-hole oil change
And a number of various other little items.
He came down to $4,800 and I think that's fair. I'm going to get eyes on it Thursday when I'm in his area for work.
7 Surprising Harley-Davidson Products that Are Not Motorcycles
Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.
Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?
Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.
Engraved Rebellion: Inside Bundnerbike's Glam Rock II
Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.
Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.
‘99 Fatboy, good choice?
