In my experience, the cutter rig is designed to enable you to establish the double slot which is a great thing. On the boat I used to race on we had what we termed a jib-top #1 that we flew with a staysail. In light to medium air, it worked like a charm. We sailed circles around single headsail rigs. The boat wasn't even a cutter, it was a 70's C&C 30. The added bonus as you say is the ability to see under the jib along with the sheets being higher which helps them get around the luff of the staysail when tacking. the main difference between your rig and ours is the fact that the jib-top #1 was 150%. Alot of folks back then called it a reacher but we went to weather just fine.