Help! Where to start???
Whether you go tiller or wheel, furling or hanked on jib depends on boat size and type of sailing you''ll do. I strongly disagree with the comment about furling being unsafe in that with furling you don''t have to go forward to take down/change sail when winds build. If you''re single handing you need to do everything you can to guarantee you stay on the boat! You simply reef to what you need from the safety of the cockpit. Of course the heart of this is a reliable and well maintained furling system that doesn''t jam. The advantage of hanked-on sails is that the cut is more efficient and you don''t have that wad of rolled up sail creating turbulence. In other words for racing you don''t want furling if you want to perform! Also, if you race you''ll want a tiller up to 30 ft. and from 28 and over a wheel for cruising comfort. A tiller gets real uncomfortable sitting sideways and turning to look forward after hours at the helm. I don''t believe tiller pilots are not as effective (or durable) as wheel pilots (I''ve had both).
With respect to outboard vs. inboard an inboard will far outperform an outboard in any kind of chop where the outboard is otherwise screaming half the time out of the water. The inboard will have much better reverse(stopping) characterists. The inboard will be quieter. However, the outboard is easier to upgrade and maintain. I wouldn''t buy an inboard unless it was a diesel and would definitely stay away from "saildrives" which are outboard type motors extended through the hull to try to act as inboards - too many problems with these. An advantage of an outboard is that it can be pulled up out of the water for less friction and hence better speed but in racing you get penalized by your rating anyway vs. the same boat with an inboard but you are faster! Over 28 ft. everything is mostly inboard anyways. In a used boat a diesel will have much more longevity than a gas engine. The diesel is also safer in that you don''t have to ventilate since the fume are not explosive like gasoling vapors.
Evaluate what you will mostly use the boat for - racing vs. cruising and keep asking people who own sailboats to form your own conclusions.
Don''t rush into a boat until you''ve thoroughly researched it. Only buy new if you''re flooded with spare change or know (most unlikely) that you''ll never want to move up.