The most important piece of equipment on board , is you, your knowledge of seaman ship, basic sailing skills, and then intermediate and then advanced. Then getting out there and sailing, gaining experience .
Also, coastal piloting and
navigation . Signal lights and day shapes,
Vessel systems. Handing emergencies.
Marine
weather
Then gain experience out there on the ocean, on a fixed
keel type of vessel , Your lessons should be on board
boats that have many different electronic,
plumbing,
engine, etc, etc, etc. systems..
Join a sailing club or organization that has structured courses.
As to all of the other things that you will need on board, I would get to sailing first, and put in serious effort and have fun
learning. None of us will ever know it all.
Then buy a boat, after a healthy amount of
research, and continue adding to your sail bag and vessel inventory. Trust me, that list is going to be very long.
All of the suggestions by the other posters are excellent, but your skills, and being a proficient
skipper high outweighs a garage full of sailing
gear that is not being used.
Once you join a sailing club, plunk down the cash, and before your fist lesson, we agree:
1. Learn and study your basic sailing manual, and all of the other course
manuals as you proceed with your
training. But, being ahead of the power curve, and having some knowledge will help .
2. Top sider or other good boat shoes.
3. Sailing gloves for line handling, and
winch work, and handling the
helm,
mooring pickup, and
anchoring.
4. Sailing Jacket. You will be taking on spray
5.
weather gear">Foul weather gear. Important.
6. Cap or hat with a chin strap.
7. Good quality polarized sun glasses with a croakie . Sun rellection off the ocean can hammer your eyes.
8,
Charts, parallel rules, dividers, hand bearing
compass. Also a piece of line to practice your figure 8's, bowlines, sheet bends, clove hitches, rolling hitches, and please learn proper cleat hitches. We carry plenty of extra line, you are going to need it for many different situations.
9. Read as many books on sailing instruction,
passage making, and first person experience authors.
10. Leatherman tool. channel locks, and good
rigging knife.
I do not know if you are U.S, or another country, so will stop here . You will need
navigation systems, buoys, navaids, lights, etc., for what ever areas that you will be sailing.
You absolutely have some great suggestions, but none of that is going to do you much good if you do not know how to sail, or ever buy that boat.
Living your sailing dream takes effort, and perseverance, study and practice, and gaining experience . And then fully understanding a skippers responsibility. It is huge.
" The ocean does not love you, any indifference toward her, and she will kick your transom, big time. "