Unfortunately question 4 is the most pertinant question for this type of boat. Moorings are extremely expensive and tightly held in Sydney harbour and you will not get one in your lifetime. Liken it to MCC membership, you put your children down for membership before they are born so that their children may arrive at the front of the que. The Hood 23 may well be a mooring minder ie a boat that is used to hold a mooring for the licensee until such time as their new boat arrives.
Better to take up option 2 before buying a boat, a lot of opportunity for sailing may open up to you by joining a yacht club.
Cheers

What you say frant about moorings is true for Watson Bay, but if go right back towards Parrammatta you may have a better chance.

Ask the RMS, only they can tell you what's available.

Hood is a good boat. You can get away with a much lighter engine than 6HP btw. Other one to look at is a fiberglass Folkboat ... fractional rig, wonderful manners, easy to sail & better looking than a Hood, great sea boats so you can sail it up to Pittwater for the weekend. Look for a boat that is being sailed and used rather than one that is a mooring minder & nothing works. Ask how long since standing rigging was replaced and factor replacement into your purchase price.

Regarding govt moorings you'll have a long waiting time for somewhere like Snails Bay in Balmain but pop down to Waterways in Rozelle. They have a map on the wall showing waiting times & there's heaps of areas on Sydney Harbour with zero or low waiting times.

Thanks everyone ... I must say, this is a fantastic forum and already getting me hooked to sailing, at least arm-chair version
Thanks for some great advice!! As a newbie deciding whether to dip my toe in it or not, this is a great start.

Go to the Roads and Maritime website and look at the mooring maps and waiting lists. If your boat is on a mooring, ere is a chance you may be able to transfer it to your name. But, a private mooring in Sydney Harbour is NOT expensive, if it's a swing mooring. You will pay about $400 a year for the license, plus about the same for a service of the tackle. You will also need to put the tackle down if there isn't any on the spot that you can take over.

As for the boat, a good solid Top Hat will set you back about $10k, or perhaps less if you're prepared to have something a little less well looked after. Compare this to a Hood and you'll soon realize that the Top Hat is a far better bet. So to are the Folkboats, Endevours, Compass etc. especially if you want to venture outside or have more than a couple of people on board.

Four years ago I went through exactly what you're doing now and the Top Hat was my choice because of its full keel, full fiberglass and the fact that they've circumnavigated the world.

Have fun in your search!

Certainly doing a course is a good idea, there are several stages you can complete, Introductory - learn to sail, competent crew and bareboat skippers. Sydney Harbour is an expensive place to learn - Pittwater offers cheaper alternatives.

I was in a similar situation to yourself about 4 years ago and was keen to buy a yacht. On further research I realised the initial purchase cost and ongoing expenses outweighed the total usage I would get out of the boat, So I decided to enter into a private boat share / Syndicate with 2 other sailing enthusiasts at the same experience level as me.

We bought a compass 29, very stable seaworthy vessel and great for introductory sailing and cursing on Sydney Harbour. We have had 3 fantastic years in the 3 way boat share and now one of the partners is looking to leave due to other commitments. Consequently we are on the lookout for a new partner to join our Syndicate. Let me know if you are interested to hear more about this very affordable opportunity (beginners welcome,"we can show you the ropes") . The Boat is kept at Mosman and within immediate access of the main sailing area on Sydney Harbour.