I've been there a few times and to be honest I wouldn't attempt crossing Breaksea unless with another vessel who knows the area for the first few times. I see Lucky Phill crossed at zero crossing recently but that needs calm seas, I've never been fortunate to get the tides and wind to coincide. Fuel is a consideration, 60km just from Urangan to Roonies for an anchorage then from there on too many options depending on weather.
There are plenty of areas inside HB that will fish well as well. What is your range fuel wise.