Looks like hes got a boat that will handle anything that he'll encounter in any tide going Okisollo /Hole in Wall route.
As long as hes capable at the wheel of his vessel and no mechanical problems.
The run up and through hole in wall..and ive done it many many times at all different tides in different boats(smallest was my 552 Campion Explorer in worst possible tides/winds)..can be interesting, but it is the most scenic, its the only way we go to Little Dent.
One of my favourite runs
Worst water conditions I've run into in all those trips so far was heading up Discovery Passage,bucking the tide and wind..praying for that right turn into calm waters of Okisollo ..lol
Check wind forcasts and tides,web cams and call Browns Bay before you head out if your really concerned...most if not all plotters will give you the speed and direction of tides you want to lookup.
I always launch in CRiver in behind Superstore..great ramp.
I love seeing the force of the ocean in some of the places along the way.
Depending on tides
Cooper Pt,or Owen bay side,entrance to hole in wall, Yuculta rapids,Gillard passage..
When you get up there the Dent Rappids and Devils hole..soo cool..
Enjoy your trip