Never done an october crossing but I did to a late August - September crossing last year, which was indeed nearly suicide. We ran smack into Hurricane Ike in it's formative stages.... offshore whoever even a hurricane is navigable if it's not full strength, 3 days under bare poles making 6+ knots... not fun at the time nor something I would like to do again but definitely an unforgetable experience...
The Azores high will probably be a bit large in October so my only recommendation is to not be in a hurry or to take plenty of fuel... otherwise, have a great trip.
“The world turns aside to let any man pass who knows where he is going.” (Epictetus 55 - 135 AD)
"To see new things, and live day to day, is better than wine or poppy, and fitter for a man." (Theseus)