I don't think I'd pick either of those as a first bike, but if it has to be one of the two, I'd go w/ the Honda. Newer, and should be less to repair in the even that you drop it.
Anyone have real experience with either of these bikes? I'm looking at a 91-95 carb'd 900SS/SP or a 98-00 VFR800i. I'm a new rider and want to eventually carry a passenger and a small amount of luggage for weekend trips. I'd like to get something sporty but not race-replica. I'm not shy about doing maintenance myself, so periodic adjustments aren't a bother. Catastrophic failures are a concern.
Is there a good reason to pick on over the other? Used prices are comparable.
And yes, I'm taking the MSF course.
IF you choose the 900SS, the desmo valve service is recommended every 6000 miles (at least on mine it is) and they generally run $7-800 at a dealership but there are plenty of people out there who do their own: http://www.ducatitech.com/2v/maint/adjust/
Look up the desmodromic valve-trains if you get a chance. Neat stuff.
Having owned and maintained variants of both the more logical decision would be the VFR. I think that you give up little to nothing by choosing the Honda in this case and the resale of the VFR at this point is phenomenal.
The Ducati is a solid choice but for sport touring the nod goes to the V-4.