HELP! Where to start?
Once again, Jeff has provided some excellent advice and I agree with him on most of his points. The decision between a wheel and a tiller tends to be a very personal one. Die hard sailors will generally agree that sailing will a tiller in hand gives alot more feel for the boat, the set of her sails, etc. While I agree that the tiller gives a much better "feel," I think that a wheel is alot more convenient. Depending on the boat, a tiller, due to its arc, can eat up alot of space. With a wheel, you can mount instruments such as a compass, gps, chartplotter or even a radar screen much closer to the helmsperson. I singlehand more frequently than I would like to and I would strongly suggest an investment in an autopilot. While autopilots often get a bad rap, in a vast majority of situations (weather, sea state, and otherwise) they give you the ability to do other things such as raise/lower sails, goto the bathroom and the like. In addition, in normal conditions, an autopilot can steer a good compass or gps course. They are convenient and you will feel alot less fatigued on longer journeys. I would strongly disagree with Jeff on the roller furling system. I have had various Profurl systems on my 26'', 30'', and, current, on my 34'' boat. If offers the convenience of having only one headsail, can be reefed down to nothing in a blow, and saves you from going to the foredeck to wrestle down (and put up) the jib. It would (and has been) at the top of my list to any boat that did not have one already. The diesel/outboard question comes down to cost. If you can afford the diesel, I would strongly recommend geting one. You need an engine the most in the worse conditions. In big seas, an outboard is of little use as it comes out of the water and the prop spins freely. I agree strongly with Jeff on the new or used question; I would save your money and go for a very good used boat. With a used boat, you can get more boat for the money, save yourself from the huge hit on depreciation from year 0 to year 1, and have money left over for upgrades, sailing lessons, etc. Good luck.