My Basso does not have much clearance, but I can squeeze Crud Road Racer mudguards on and leave them fitted all year round. The Cannondale has more room so the Cruds would be a better fit on that bike, but the parts on that bike cost a lot more than those on the Basso so I would rather not expose them to more muck than I have to, guards or not.
If I could afford it, I would retire the Basso and replace it with an audax/light touring bike with proper SKS mudguards and a rack. I'd probably choose titanium or 953 steel for the frame.
I like the Cannondale, but if money were no object I would probably retire that bike too and replace it with a carbon fibre best bike. That bike would be as light as I could make it without going mad. 6.5 - 7.0 kg would be nice. (1.5 - 2.0 kg less than my already lightish Cannondale.)