It's a great trip to do Alex. I did it last year in my (fast) 2 seat ultralight. I planned the trip (from the Hunter Valley) for June & monitored the wx for weeks to get a feel for what was happening. When a window appeared I went for it. Home to YCEM 1st day, then YCEM to a private strip across Ralphs Bay from Hobart, stopping at Flinders Island for a not really required top up of fuel, then down the east coast of Tassie. Returned 2 days later doing the inland route up towards Launceston skirting to the west of the CTA on to Devonport, then tracked to Wynyard to refuel. From there tracked along the north coast to Smithton then tracked to King Island, but didn't land there. Continued direct to Apollo Bay then did the Twelve Apostles fly by then to Ballarat for fuel.
Used the maximum altitude possible (8,500'/9500') across the straight, wore the mandatory life jackets & did 10 minute reporting to Melbourne Centre across the water.
I'm sure others that do/have done it more regularly can give you a lot more good advice.
Enjoy!