A long list of expectations for sure. Take a look at Vstrom 650, but that is probably more than you want to pay. KLR 650 fits most of your criterion, economical to operate but is not "quick". Suzuki M50 is cheap comfortable and economical and handles well for a cruiser. If you have stuck with the 250 for three years, I suspect "quick" is a relative term. Go Big. Vstrom 650 with abs. All the bike you will ever need.
I have pretty much all the same requirements of a bike (minus the roll on wheelies, but I'll take em if I can get em), and I've been extremely happy with my DL650 V-Strom. The 07s have ABS available. You won't get the roll on wheelies (except maybe in 1st), but it's easy to clutch up if that's your thing.
If you're willing to spend a bit more and compromise a bit on the running costs, the new Triumph Tiger, the Multistrada, the Buell Ulysses, or maybe even an FZ1 will all lift the front quite easily. You're going to pay for it in gas and tires though.