Hi Brett - you will just love the Whitsundays. Our boat, a Catalina 380 has travelled from Sydney to the Whitsundays three times and every cruise was absolutely fantastic !!!
Our Catalina is not known for its blue water capabilities but up and down the east coast of Australia it has been great.
When are you planning to leave ?? If it's within a year or so why not just go and buy the cat you like and learn to sail on that.
Cruising the Whitsundays is not that taxing - there are numerous safe anchorages for any wind direction- you just have to keep an eye out for the reefs.
I'm all excited now after hearing your plans. I think I'll start work on my hubby for our next trip ....