Within the current (say from 2000) big twin lineup there are three series, Dyna Super Glide (FXD), Softail (FLS), and Touring (FLH). Tourers are pretty easy to recognize with their larger fenders, luggage, and some form of windshield or fairing as standard. Softail’s and Dyna’s can appear similar, the easiest way to distinguish them is Dyna’s have two conventional rear shocks. Softail has a hidden single rear shock. Dyna’s look like a longer, lower Sportster.
Dyna’s and Tourer’s share the same engine and transmission which are mounted as a unit in the frames with rubber isolaters a la Norton. You feel the vibes at idle and low rpm but they actually become smooth at highway speeds. Softails use a “B” version of the engine which has a counter-balancer built in so they can mount it solid and very close to the frame. B engines are smooth at idle and up to normal road speeds but develop a bit of vibration at higher speeds.
2000-2006 used the Twin Cam 88” engine (1450cc). 2000-2002 are considered good years in they still used Timken bearings in the bottom end which tended to hold up better for people enlarging the engine for more power. Otherwise the newer bearings hold up fine. For Dyna’s fuel injection was made available as an option starting in 2004, and it works well with typical FI benefit. But carb’d engines are fine also.
For 2005 HD redesigned (improved?) the valves with smaller stems or something. But the result was many 05’s burned oil. HD has a service bulletin on this and many had their valves replaced under warranty. Something to be aware of if looking at an 05, just check the service records and ask about oil consumption. For 2006 HD fitted their all new 6-speed in the Dyna, which required some changes to the primary. The 06 primary re-design was not good and the inner primary bearings routinely fail. Personally I would avoid an 06 Dyna.
2007 saw the 88 engine replaced by the substantially changed and improved 96” and improved primary but at this point the resale values may be inching beyond what you’re looking to spend.
Although the 88” Twin Cam is considered a very good engine he shortcoming with all 88” engines are the spring loaded cam chain tensioners. At some point, typically between 25,000 and 60,000 miles, the plastic slider shoes will wear thin enough to break apart. The remaining metal backing maintains tension so you do not hear or feel anything, but the chunks of plastic end up lodging in the oil pump and starve the engine of oil which can ruin pretty much the entire engine. The reason there’s such a wide spread in mileage when they fail seems related to when the chains were stamped in relation to when the tooling dyes in the presses were replaced. Chains varied between some being somewhat rounded or polished, while others were more sharply cut. Just the luck of the draw.
The good news is the tensioner shoes can be inspected w/o too much trouble and any HD mechanic will be well aware of it and have the procedure down pat. If they need changed the newer ones will last longer simply due to the fact the chains have polished themselves from sliding against the original shoes. HD also offers an upgrade kit which replaces the spring system with the improved hydraulic tension system used in the 96” engine. As a side benefit it comes complete with a higher flow oil pump.
There are different levels of fitment in addition to the basic FXD with a single seat, no tach, mill finish aluminum cases. FXDC (custom) has more chrome, double seat, etc. My favorite Dyna is the FXDX (Super Glide Sport) 2000-2005. It’s raised up with better suspension components F&R, blacked out with almost no chrome, dual disc front brakes, speedo and tach mounted where you can see them, lower bars, and mid mounted foot pegs. My understanding is these were somewhat popular in Europe but were extremely slow sellers here in the U.S. 2005’s were showing up when I bought my 2004 FXDXI as a discounted leftover. I still have it. The upgraded tensioner setup was installed in it three years ago.