I have both, a 550 & a 750, and love them both for what they are. Here are my thoughts:
The 550 is a med sized bike, relatively lightweight. It is easy to push around the garage, very fun to ride, is very nimble and loves cornering and accelerating up to 9k rpm. Fun!
On the negative side, riding on the highway at 60 mph and being passed by a semi makes me a little uneasy. The bike is light and you can feel the air wake from the truck move the bike. This made me sell my 550 a few years ago and buy a 750.
The 750 is a great bike, legendary! It's a full size bike and rather heavy, which is good and bad. Pushing it around the garage, I have to be conscious that don't lose control of it (hasn't happened). The bike is fast, although my current 750 is actually an 836cc. It handles well, but doesn't feel as agile as the 550. It is very fun to ride and feels very stable and sure footed on the highway, great for a trip.
If I was told I had to choose one, I would say no, I don't have to, I want both!
When I sold my 550 a few years back, I missed it. So I bought another, actually 2, I now have a K & F model, although the L model is not roadworthy yet.
My suggestion is to buy a 750 but keep your 550.