You ask some good questions, but they're all in the world of "it depends."
I recently bought a boat that had been raced, in part because it had an extensive sail collection (several very recent) and the standing rigging had been replaced and upgraded not long ago. It was also came with with two spinnakers, whisker pole, and other race-related controls. These were all pluses for me, as well as the fact the rigging had been kept tuned and maintained well.
On the other hand, I'd stay clear of race boats that haven't been well maintained, old standing rigging, tabbing coming loose below decks, leaks or stress cracks from over-tight rigging, etc.
As for tiller, there's reasons pro and con, but it's often a matter of personal choice. An argument could be made that there's no real mechanical advantage of having a wheel on a boat that's less than 30-34 feet, and there's a mechanical disadvantage in that a wheel may be more complicated to service and maintain compared to a simple tiller. One gets less feedback from a wheel, and in my opinion it's harder to add an autopilot to a wheel.
For a single-hander, it might be nice to just tighten the knob on a wheel to hold it in place while doing other jobs. A tiller can be locked pretty easily with a basic auto-pilot, and I really liked how the previous owner installed the tiller pilot on our boat (and it can steer to waypoints on the GPS).
Finally, based on the design of the cockpit on a small sailboat, the wheel could be a pain or benefit for climbing around when managing sails and the like. Some tillers "sweep" the cockpit and can be a pain, but they also can normally fold up and out of the way when anchored or even changing tacks. Some wheel set ups can be pretty inconvient for managing sheets and moving about, depending on the cockpit setup.
If you haven't guessed-- my bias is for a tiller, and others might sucessfully argue a wheel is better. "It depends..."