There are no portuguese trades in May. You are mixing up information.
The "trades" blow hard June till about end of Augus. Give or take.
Must be aware going early is not a good option either - till about June lows pass very close to, over, or just below the Azores, bringing nastiness, cold, rain and (to you)heading winds.
You can make a smaller leap to the Madeira, the look again at wx data, then jump on to the Azores. This is easier as the time slots are shorter and thus the wx
forecast will be more reliable.
At ANY time of the year, have the
boat and yourself very very well prepared. Mind you can get a bad storm on this route at any time of the year.
It is easy. But do look at the wx very closely and do NOT go if you see a train coming. They move at intervals - 5 to 10 days between them (vs a stationary object) so just watch them well and go when a mild one comes and when its track is not expected to get over, or to close to, the islands.
The Azores are a beutiful place and people there are very nice.
Food is excellent. The
weather, in the summer, tends to be excellent (if with a high % of calms).
Have fun.
b.