Well, they're really two different bikes. At 30-40 mph the 1000DS will walk the 749D, and 'prolly my 749R racebike too. However, once the 749D spins up, it'll be gone.
The weight is not that different, but the 749 will feel a bit lighter.
Regarding price, the 1000 is cheaper, and is less expensive to maintain. However, the 749 will be worth more a year from now. The 749D is actually cheaper, however, if you consider the additional expense of the additional mechanical sophistication (engine / suspension, etc.). As you mentioned...4 trips to Starbucks.
The paint scheme on the '05 SS is awesome...basically it's a "Senna" bike. The red wheels really set off the charcoal paint nicely. It's a really pretty bike with a lot of style. The 749 D also looks awesome. In that dark color, it has a bit of a menacing look to it. Every time I rode my demo around, people would ask..."what's is thaa...that's a Ducati?!" The paint has a metallic to it while still actually being flat. It looks fast and radical.
Regarding the "B-aah-ch" appeal, the SS is significantly more comfortable if you're actually going to take a passenger around. The 749D, however, is more likely to get the pillion on there in the first place! Some consider the 1000DS to be a bit of an "old man's bike." However, it sez "Ducati" on it, which apparently sends da "B's" flocking!

Dirty little secret...besides my MH900e with Staintunes, the best sounding Ducati's are the air-coooled models with low pipes! The 749D sounds awesome and like it means business because it does...the 1000SS booms! Lovely.
Joy of riding experience? They're the same and different at the same time. The SS is made to run through the canyons from one cafe to the next. Fast. Relatively comfy. The 749D is a Superbike. Although it's got no damper (not a huge loss), it's meant for the canyons and the racetrack. If you're going to do track days, the SS will work great, but it'll get worked but the 749D. Ergos on both are surprisingly similar, and can be changed easily with bar risers, and if necessary, rear sets.
Send me an email at
sales@section8superbike.com if you have any more questions, or would like me to expand upon any of the opinions expressed above. We've sold out of both out '04 1000DS' and 749D's - I'll be happy to put you into the bike that most suits what you really want to do with it.
Let me know and we'll go from there.
Bill "where'd my section8 banner go?" Keros
section8superbike.com