There is a Pearson Vanguard on my pier. A guy singlehands it all the time and is always out in the snottiest weather and just loves it. I have a Pearson 28 (1976) and have a better interior lay out, longer water lline, shorter LOA, same beam, 6 inches more draft. I can go faster and closer to the wind and have better manuverability with a more responsive rudder. So, what I'm saying is that the old full keel/barndoor rudder boats that are long and skinny with big overhangs (beautiful as they are) do not sail as well as newer designs with modern underbodies. Also my shorter LOA means I can go into a 30 foot slip, instead of a 36/40 foot slip and pay less $$$ every month. Same pier. Not only that, but for much less that $20,000 I have a solid hull with new sails, roller furler, standing rigging, running rigging, fuel system, sewage system, berth cushions, tiller pilot, and stove. No diesel, but then I don't think I want the smell and noise of a diesel just to power out of the slip, up the sails and shut it down before it even warms up. Look around really hard with no preconcieved notions and you can find a really good boat for the type of sailing you want for the money your are quoting. I reserved half of my budget to repair and replace old equipment which I've done over the last few years. Good luck,
ps. Regarding wheel steering. Have you noticed that the wheel puts you at the very back of the boat where movement and exposure is greatest? With a tiller you sit or stand more forward in the cockpit taking shelter from the weather and be in closer proximity to crew for conversation/communication?