Rick, You did not mention if your "two up" sailing would include racing. My experience is that this makes a significant difference in choosing a boat. Jamie is giving you good advice to consider an A-cat if you want a fast boat to "retire" with as long as you will race it single-handed only. My wife and I have sailed our A cat together and as long as we do not push it then we do not need to be concerned about the issues that Bill Roberts described earlier. In fact, our Boyer Mark IV is so light and narrow hulled that it is easily the smoothest sailing boat we have ever experienced in the Lake Erie chop. So far we have hiked and trapezed together while flying a hull but I would be unwilling to put a second trap on the boat even with just our 300# combined sailing weight. It is a joy to rig and move due to its light weight but that also makes it a nuisance because I have to take the mast down in any wind over about twelve mph as it may blow the boat over and/or the 6" x 30' carbon mast pumps (rythmic shaking) which is undesired to unnerving. Since I normally keep my boats rigged on the deck at the water's edge for quick launching, this makes the "A" more high maintenance and therefore used less often (we also have a Hobie Wave and a Mystere 4.3 ready to go that are fine with the rigs up in any weather that we have had so far). If we race together, which we did once, then the wind is light to medium so that we do not stress anything and that means we cannot sail to the boat's PN numbers, especially off the wind against the spinnaker equipped boats like the Taipan or I-17. So if you race by yourself, no worries. And rec sailing will most likely be as Jamie suggested anyway - in wind conditions that will not overload the boat's design.
So I understand what you are looking for, especially if you want a fast boat that is equally good at racing fast single-handed or double-handed and really especially if you are looking for a boat under $10K. There are few good choices. Please share with us what you end up with and how you like it.
Mike Fahle