Muogamarra reserve. only open in august for 4 weekends or so. Brooner did it last year i think. Can probably do that with taffy's.
I'm keen for most of the local stuff you mentioned.
I'm also keen for the local runs once I get my health and fitness back...
Add in the Sydney North squash run, mostly via trails: Thornleigh -> Marsfield -> Mac Uni -> Lane Cove - Willoughby - Norths. Approx 25km. For extra difficulty include a game at each venue and/or in reverse direction for more climb.
We can even extend that to a full marathon starting at TLC, Baulko then trails to Thornleigh. Stan as support crew in a car and make it a game to 21 points with round robin format eventually leading to a final at the last stop.
That local Sydney run around Kosciusko...
Also drive to and run all the out-and-backs along West Head Rd
*Drive to start of road then bike*
I'm not taking on Mona Vale Rd again
Glenbrook to Katoomba
Baulko to Brooklyn
Blackheath to Richmond http://gnw250.com/trip-report-blackheath-to-richmo...
Full RNP loop (50 or 70km option)
Not Sydney but very cool and remote loop from Point Lookouthttp://www.movescount.com/map?route=3644531&la...