Kankama said..Some random thoughts in the short time right now.
One month Eden to Airlie may be a bit short but it can be done. But why the timetable? You will have much more fun if you have a destination but not a time OR a time and not a destination. You should NOT have both if you want to have a good trip.
If you want friends to come then allow them to select a time and then you say "About a week out I will let you know where to fly to". Don't tie yourself to a time and place and have friends flying in - bad news and stressful if the wind starts blowing hard the wrong way.
The Whitsundays are nice but make sure you start cruising as soon as you cross the Wide Bay Bar - I recommend new sailors fly their more reluctant partner and family up to Rainbow or Tin Can and gently potter around the straits and Platypus Bay for a week getting sea legs. It doesn't get magically better after Sandy Straits - everywhere is great - if you have the mindset.
Keppel is great for walking - almost no islands better, great beaches, but not so much coral, so you walk and swim there. Island Head is remote with huge beaches so you walk and have great fires on the beach cooking potatoes there - but you don't swim - crocs perhaps.
I like to think of the NSW coast as a delivery - your boat can only get you to one spot - Broughton - you can't get to by car. So if you are looking at getting some mates on board - get them to do this with you and just get sailing. Have a rest at the Gold Coast (but with your draft maybe you will be keeping to the channels) and then plug up to Wide Bay where you can slack right off. No reason to go to the Whitsundays - they are great but it is better to have a great trip and turn around at Percy (I love Percy but I can dry out in the lagoon) rather than turn the trip into a delivery trip special - all deadlines and no fun.
We almost never night sail - our cat can average 7 knots easily (usually about 8 on the chart) and she surfs very well too. So we can plug in about 70 miles fine and just surf in if the bar looks a little dodgy. But you may not have the legs or the bar crossing ability to do that. From Eden you have Bermagui (bar okay) Batemans Bay - no bar to stay in the bay, Jervis, new marina near Kiama, Botany Bay, Sydney, Newcastle, Port Stephens, and then a big one - Broughton to Camden Haven/Port Mac if it is nice or Coffs. Yamba next and then maybe all the way to Gold Coast.
Go when the weather is good and stop when it isn't. Use Windy and BOM to plan your days a few days ahead so you stop one day early or push ahead to get to a nice spot rather than end up say anchored in Coffs in a huge blow - much better to be in Iluka and be able to get off the boat. (Although Coffs marina is fun in a blow - if the marina is safe)