While nicely stowable, I found that rollups are just too much of a PITA to assemble/take down on deck and don't take the weight/power of higher HP outboards. I prefer a bigger outboard than 2-4HP because a) I like to get where I'm going and b) have enough power to bore through waves on a plane. Also, rollups (esp those with High pressure floors) are too 'flexible' & 'twisty' for my taste (my HP floor Zodiac almost folded back in on itself in a big chop).
While I love the idea of a shippy looking rowing dinghy (i.e. fatty knees, etc.) they are just too tender for me. I like the stability of an inflatable.
I now have a Hypalon Apex 9' lightweight RIB (Apex A9-L). It stows with the transom butted against the mast and the bow falls just short of the Sampson posts. The reason I like the Apex is the tubes are not the larger diameter (ala Caribe) and thus not so wide you can't get around it to the foredeck. I like it so much that I just priced a new one ($2799 in Central America) since while still serviceable it's getting along in years (10+). It's powered by a 8hp 2 stroke Yamaha Enduro.
Both dinghy & outboard are pretty easy to get overboard by myself via a 3-1 tackle I hang on a halyard. And easily/safely towable even in 4-6' seas preventing it from having to be unloaded/unloaded all the time.
Finally if you are, or plan to be in the tropics (as I am) I definitely recommend getting some sunbrella 'chaps' made. IMO a dinghy cover probably extends the life of a inflatable 2X.
Bear in mind my requirements are set by the area I usually cruise in (Belize, Honduras, Mexico), i.e. constant 15-20 kn trade winds with normally 2-4' seas. And that's a calm day. Your mileage may vary.