I am 65, retired, and live on a pension so I really have to watch my pennies.

I have also been a motorcycle rider for 50 years, off and on, and my last bike, before a 25 year hiatus was a HD FLH that I had to sell for financial reasons.

This past summer I picked up a Honda 750 but, frankly, it never felt quite right so I started looking at Harleys again.

I sat on a 2008 Dyna Low Rider at a local dealership and it felt perfect but it was well beyond my price range ($12k)

I went to another dealership to check out a 2002 883 they had at a bargain price ($4k) but found it to be WAY SMALL, or at least it felt small!

They also had a 2002 FXD Super Glide and it felt right! They were asking $1k more than I was comfortable with but I may call them back and try to negotiate a better price.

Today I am off to look at a 1997 Sportster that is dressed pretty much the way I like and the price is within my range but I wont have an impression until I sit on it.

I really like the 2002 FXD and it is hard to "be practical" when I like something! Whatever I do will likely be the last bike I ever own and I will be paying for it for years.

...... tough decisions!

Suggestions welcome!

 

Keep looking until one "speaks" to you. If it is the Dyna maybe check your local Craigslist ads to save some money over the dealer's price.

 

Find something you like and can pay cash for it. Please don't make payment plan for such an old bike at 65.

 

I have no children and no heirs so the government will get a big chunk of anything I leave behind. My goal is to die as deeply in debt as possible!

 

you already found the sportster to be too small. it didn't get rained on and grow any.

 

In the northern climate, this is the best time of year to buy a bike. Look on Craigslist.....you'll see many garage queens for very little money. Take your pick.

 

Yep I agree, stop looking at Sportsters. A nice Dyna will appear at the right price if you're patient.

 

In that case go for a brand new CVO.

 

Like the others said, if you already feel a Dyna feels right, you'll get tired of a Sporty really quick. Craigslist is an option. There's also Cycle Trader. You'll probably be happier in the long run sticking with 2008+ so you get the 96 ci engine if you can.

Here's a few suggestions to save some cash on the initial buy ...

• Private Sellers ... dealers mark stuff up for a profit and are rarely "motivated sellers". Sometimes individuals just need to get the bike sold. A little more risk, but if you find an honest person and can wrench a little if something does go wrong, you'll probably get a much better deal.
  
  
• If you go to a dealer, don't go to a Harley Dealer. People go to Harley dealers for Harleys, so they have little incentive to cut a real deal. Honda (and other) dealers have little desire for used Harleys to sit on their floor. When I was shopping, I found better prices and more willingness to negotiate from non-Harley shops.
  
  
• Check out your indy repair shops. They often have consignments or know about customers that are selling bikes.
  
  
• Think about getting a bike that isn't yet "dressed pretty much the way I like" but is more stock and less expensive and adding parts over time. That's what I did ... getting parts from eBay, HD Forums and local swap meets. I eventually found stuff like a mint Sundowner Solo for $12, an engine guard in acceptable condition for $25, a Badlands unit for 1/2 of retail, etc.
  
  
• Where are you looking? Not sure how prices are in Manitoba, Canada, but maybe you'll find a better deal in ND or MN? Drive down w a friend and ride it home. Maybe you find a great deal and a great first adventure on your new bike all in one. I bought mine out of state from a private seller and rode it home about 2 hours in 27 degree (fahrenheit) January weather ... cold, yeah, but got a really good deal.

Number 1 suggestion - be patient. The right bike at the right price is out there. It's almost winter in Canada. Not like you'll get a ton of riding in for the next few months anyway.

Good luck.

EDIT - BTW, $12,000 (assuming CN dollars) is $10,700 US. That's on the high side for a 2008. There are a bunch of 2008 Dynas on Cycle Trader for between $5000 and $10000 US right now. Maybe it's worth thinking about buying a plane ticket and riding it home.

 

Okay, I'm an older rider like you and I'm just going to throw this out there. But for the money your spending would a used Road King fall into that price range in your market? You liked the FLH in the past, and I have ridden a dyna recently and you would be so much more comfortable on a King. Even if you don't intend to tour, the RK is a great around town bike.

Just throwing my two cents in there.