It's not late for Lake Ontario
, but it's problematic for the canals, etc. You can't travel as far in the reduced hours of daylight, and there will be fewer places to fill up, and maybe longer waits for locks.
Then, once out and down the Hudson, you are still in late hurricane
season going down the ICW. If you get a decent weather window, you can go "outside"...but it's not what I would recommend to a first-timer on a 33 footer. You need to be aware of fishing
fleets, Gulf Stream
counter-currents...and how long it would take you to get back "inside" should conditions crumble in a fall gale.
By the way, that go south primer is pretty good and Wallace Gouk has a good reputation as a surveyor
around here. If you pass Toronto, you might wish to commission a "fitness survey" for your Hunter
to determine if you've covered all the bases.