My boat is in that range (27') where it could be a tiller or a wheel ... and it was sold both ways, (with a balanced spade rudder forward of the transom). I've thought about changing to tiller steering, but I think it would only be suitable if the boat was used strictly for single-handing. The cockpit is simply too small to accommodate the shifting around that would be necessary when tacking or jibing over. Plus, I find that with the winch positions being aft and the bridgedeck-mounted traveler, the lines are more easily managed from behind the pedestal. Far more were sold as wheel-steered, I believe, based on re-sales. (Perhaps the tiller-steered versions were junked!)
But that does lead to my problem ... I like to sit aside the wheel and even slightly forward, in a position where I would sit if I had a tiller. With a smaller diameter wheel, I can climb around the wheel (T-shaped cockpit - also designed for wheel) more easily, but I would like a larger diameter wheel to make the reach more comfortable.
In the end, I think the wheel is more practical on my 27' boat, and was intentionally designed for it (I think). I wouldn't change it to a tiller. I don't think I would make a purchase decision based on whether or not a boat had wheel or tiller in the 30-34' range, and I certainly wouldn't think about purchasing a boat with the thought of changing it one way or the other. I think it is more likely that I would turn away from a boat in that size range if it were tiller-steered, though. I think I would find more disadvantages. Just a personal choice though, in many respects.
Scott, that's a great post. You are right, all boats are compromises, and a big one, in particular in smaller boats, is cockpit room. Many times steering choices are dictated by that, along with fashion. Wheels (in particular SMALL wheels) take up much less space. But speaking of fashion, I'm sorry but this is taking it too far. The wheel ends up being so small that the only thing you can do is stand behind it. It just does not seem to be designed to be sailed. Maybe that's just my definition
Back to bigger boats, with some planning both tillers and wheels will work. New designs have sorted out the heavy tiller/rudder feel that used to make wheels almost mandatory, and a cockpit can be laid out to work well with both. Then it becomes a pure issue of what works best for you. This was not necessarily true with older designs. And remember , boats this size would have a below-decks autopilot in either case, and it works exactly the same for the tiller as it does for the wheel.
Here is a First 36.7 with a wheel. The removable seats are taken out, and the T-shaped cockpit works. The mainsheet trimmer sits just in front of the wheel pyramid. The big wheel extends to where it can be used with the driver on the rail.
Now the same boat with the tiller. The cockpit seats can go back in, the the mainsheet trimmer sit behind the driver. With a Spinlock tiller extender the driver sits on the rail.
Our smaller boat is tiller, and our big boat is wheel. I would never think of a wheel on the First 260, and happily it was never offered. The 36.7 came both ways but in the USA the One Design rules say wheel only. If that was not the case I might have gone tiller.
If its important to you, think about resale. But you only live once. Buy the one you want.