Stripping and maintaining both old and new Ducati's for a while, I would say I'm fairly competent in what makes the new and olds tick.
Here is my feelings on Ducatis new and old, the 1098S I had was fantastic, was more than capable of long distance 2 up journeys (as 4T5 has pointed out). However... It was a pig to run below 80! Absolute pig, snatchy in low revs, aggressive torque and not comfortable. Once you went over 80 (not that I ever did...), the bike was something magical, truly. It handled like nothing I have ever ridden before, it went like the clappers.
Those on that meetup 4T5 is talking about knows all too well just how quick and capable that bike is haha. Way above my limits!
But, it was expensive to buy, insure and maintain! Yes, it had a longer gap between services, but still pretty expensive. Plus, hard to maintain your self (like I did) because the garage would need to reset the trip counter for the service. Oh, and the new Ducati's have plastic tanks, older have metal.
Now, older Ducati's, that is what I fell in love with and still am in love with. My 748's were not powerful, not crazy. But jesus they were fun to ride, a ton of character to boot as well! Dead easy to maintain, simply because up until the 749/999 and the new Multi/Monster era. Ducati's were built by people, you could strip the bike in 15 minutes. Without fuss. It was a wonder to work on.
I found my self on weekends when it was raining simply stripping the 748 of everything leaving just the engine in the frame to clean and care for everything. This was both enjoyable but also plays a big part in my next motion.
Maintenance. Older Ducatis require a **** ton of love. Not a weekend toy or commuter without a lot of love. I commuted for 2 years on my 748S. Sunshine, rain, sleet and snow. At the end, I had to get the engine rebuilt. The crank had gone, rockers were worn and a few other bits had given way. Nothing I could have prevented. Well, I could have rode like a new born every day... But I worked in the country side
So, my advice would be, a new Ducati, 848 would be ideal if you just want fun, little character and maintenance free. They are fine. Infact, on par with IL4's if I'm honest. Look after it like any other bike and you will be fine. The electronics stuff is just a bad omen due to older Ducati's. It's no longer an issue.
If you want something to love and cherish for years to come, buy an older Ducati, 916, 998 if you have the money. I prefer a 748 as it revs more. They are not powerful at all compared to todays bike. But it's more than enough for the roads of today. I had so much fun on my 748, nothing has come anywhere near close to putting such a smile on my face.
Any questions, just give me a shout.
Also, to what Matt is saying, is right. Ducati's, while the newer ones, even the 1098S I had, don't require much attention, it's probably more than your average rider will put in. So many times my mate was confused by our conversations:
Him: Plans today?
Me: Clean and lube bike up, check the usuals
Him: You did that last sunday
Me: 80 miles done in that week...
You need to know what to look for, when I sold my 748S, the guy who came to saw it was with his mate, a mechanic. And no word of a lie, both their jaws dropped at my bikes. Particularly the 748S. Both of them had never seen a older Ducati look so pristine and well preserved. Even more shocked to see how many miles on the clock. Then even MORE shocked to see blisters on the tyres. Knowing I wasn't a mantle piece owner. Owning a Ducati will mean it has to be looked after a lot. But it will show

They turn heads.