HI Mate, Congrats on the buy, I was in the same spot 18 months ago, asking the same question on this forum. I bought an 18ft trailer sailer and this is what I did:
1. Tried to sail myself, snapped the mast before I got it in the water, was actually a god send as everything was rigged wrong and the accelerator cable snapped the first time I took off, would drifted into nearby rocks on my first launch which would of been worse than a broken mast.
2. Did a 4 day discover sailing course through my local yacht club on 18ft race boats with my partner, it cost about $200 each but was worth every penny.
3. Went home and re-rigged my yacht now I know how it was suppose to work, previous owner never sailed it, tinkered with it, and messed everything up, to a complete novice I had no idea of this when I bought it, I suggest learning the ropes before you start.
4. Started practising just my wife and I, even on our first outing after the accelerator cable snapping, we had enough skill to sail back up to the jetty and dock without an engine thanks to the Discover Sailing course.
5. Downloaded the audio course from itunes by Franz Amussen
www.medsailor.com/sailing-learn-to-sail-lessons/6. Made an effort to practise, not just have fun sailing for our first 10 times out, we practised anchoring multiple times,, sailing up to the jetty, picking up mooring buoys, etc. Each time discussing how we could do it better, emphasis on the WE. We learnt more about communication in these drills than about actual boat handling.
7. Went out on other peoples yachts to observe what they do, not racing just meeting people at the club house going for a sunday sail
8. We flew to Greece and did the RYA Day skipper course, about $800AUD, you get to sail around the greek isalnds on a 35" yacht with all food included, was a lot of fun and a learnt a boat load, all puns intended.
9. Hired a yacht for 8 weeks and sailed around the Med by ourselves