Might I recommend when you take'r out that you take some experienced crew/guests with you for a while, and let them teach you the ropes, as it is said.
Take'r out to the Islands and anchor
out a few times, get in some bad weather
. If you ever get any down there.
And, do a few 48 hour cruises. Take'r out just for putt'n around, practice backing, turning and docking
in cross winds and currents. Learn to use the wind
to your advantage. That should give you some of the basic experiences for cruising.
A 44 can do a lot of $$$ damage to another boat, as well as your own. So, take your time when in close quarters. Book learning
is a good idea but there is no replacement for time on the water
And yes, hang out here on the Cruisersforum! There is a lot of experience in all aspects of sailing and maintenance