You can probably pick up a 2011 plus bike in your price range. Its almost end of riding season, search craigslist and cycle trader along with ebay. Would highly recommend a bike with the 103" power pack, abs , security and plus it'll have the new frame. I picked up my bike from a local ebay listing, met with the seller and purchased it at trade in value from what a dealer was going to give him.

I purchased a 2011 street glide and love it! Wife doesn't ride with me and likes the cruiser style looking bikes and wanted me to sell mine to get one. Test drove a few other bikes , wide glide , rocker c and fat bob. Its a world of a difference compared to the touring bikes. I rode 400 miles round trip yesterday morning mainly all highway and felt great. Cruising about about 80-90mph no issues, just flipped cruise control on and enjoyed the music and road.

 

I would suggest a 2010 or newer. I wouldn't get the 2009, lots of posted problems in the first year of that generation.

I recently bought about 5 weeks ago a 2012 Limited for 15.7k with 11,261 miles on it. Look to see what touring bike you want, yes you can get a 2009-2013 tourer with low miles in your price range.

I started my research on this forum, and started with posts dated back to 2009 and read all of them related to the model I wanted and their problems, skipped over the bling posts otherwise I would still be reading.

First decide what is the look you are going for, what are the things you want on a bike, then do a comparison by google to read the differences. Once you have sorta picked the model, google ride reviews that will get you started on things to consider, then start reading the posts here, then when you have done all that test ride if you can a model you like.

Then to buy, I choose to go with Ebay. Dealerships will post there, seemed like the best price. You can see what the completed listings were priced at and what they sold for to give you an idea about purchase price. Ignore NADA, their prices are much higher than true selling price.

I wanted to buy from a dealership so I knew it was Harley Certified, and a dealerships is regulated and has a reputation to cover so they won't sell a known problem bike. I was also going to finance through the selling dealership and get a ESP and a few things added so it was worth it to me.

I saw some listings that individuals were selling for the same or more than the dealerships. I wouldn't even consider that, an individual doesn't have the accountability a dealership has and can't offer you what a dealership does.

I also choose Ebay due to their rules. I knew I was not going to buy locally, and ebay has a policy max is $500.00 to secure the bid then when you go look at it if it is not as described you can walk away and get your money back.

I bought the bike, got the one I wanted in the price range I wanted, at a dealership 900 miles away. I flew in rode it back over 3 days mapping a route with the most dealerships in route.

Best of luck in your search, and this a good time. There is a flood of pre 2014 bikes available and riding season is nearing an end in a couple of months so dealerships will want to get the pre 2014 out since the 2015 have now just come in.

 

Second the motion on checking ebay sold listings to see what bikes have sold for. There can be some surprising differences in sales of similar bikes; if you're willing to wait a while, you can often get a good deal. These listings can also let you compare models and their relative prices, and help you narrow down your model preference and see what your budget fits.

That's basically what I did, with a couple trips to the dealer, to see what they had, and what the different models looked like in person.

 

OP, thanks for posting this question. I too am new to HD & am currently looking for an Ultra Classic. This thread has all ready helped me in my research. Thank you all.