We just want to get him started on the right track.
The sources you listed are indeed useful - I glanced at them all and will look more closely as it gets colder. Thank you.
I approached sailing pretty ad hoc when I bought the thing. How hard could it be??? Boat water float simple. Not so fast......I ended up preparing a plan of action after the first outing.
1.
Learn The Law: Safety, registration/titling, navigation, lights, waste stream, required equipment.
2. G
et A Note Book: And write in it. Often. Make notes and lists.
3.
Inventory and document your equipment. Sails. Lines. Makes, models, serial numbers, fluids. Take pictures of everything BEFORE.
4.
Evaluate condition of boat. Items missing, bent, broken. Put a hose on it and check for leaks. Crawl around and try to look at
every single inch of that boat inside and out if possible. Stomp around on decks. Push and pull things inside and out. Surprises on the water are almost never a good surprise.
5.
Learn about the subject - Sailing. Small fiberglass boats. Outboard engines. Trailering. Information available online for free - 10 lifetimes worth of reading for thousands of people. Read read read. Take classes. Take notes. There are endless checklists available online for preparing the equipment. Find them. Use them. Do your homework first and then ask others for advice. Advice is pretty cheap these days so weigh carefully what advice you receive and decide for yourself its validity.
6.
Decide Course of Action. You will have categories of lists.
a.
MUST DO. Unsafe conditions or inoperable or missing required equipment. Examples: ForeStay Broken. No anchor and/or anchor line. Tire on trailer loose. Gas can leaking. Etc. FIX THESE FIRST.
b.
SHOULD DO. Example: Left Window leaks when raining slowly filling up storage locker. Cockpit sole spongy and leaks into boat. Main Sail getting worn out. Etc.
c.
NICE TO DO. Example: V-berth cushions smelly and falling apart. Curtains are ugly and stained. A Bimini would be nice. Etc.
d.
IF I WAS RICH or RETIRED AND RICH. Examples: Add hatches in cockpit seats. Put in a big screen TV. Etc.
7.
Trailers. Make sure your hauler and your trailer are in good shape and that you know how to handle one. Practice it. Have a spare tire.
8.
Boat Ramps. Make sure you have some idea of how you will handle yourself and your rig at a boat ramp both putting in and taking out.
Visualize yourself doing it before doing it. Know the ramp. Think what you will do if you have problems. Be prepared.
9.
Have an Emergency Plan. A boat is a big deal. For example. Sitting on a roadside with broken truck trailer boat with no contingency plan is just asking for a really really bad day for everyone. Make sure someone off the water knows your plans. Etc.
10.
Think About It. Having and using a good size sailboat requires fore-thought, knowledge, wisdom, experience. The details matter. For example you have to think about giving someone a ride on your sailboat - ok I've got the required CG approved life jackets for everyone but now 2 guests get in for a ride - DNR stops you......oops. If you don't consider something don't be surprised when something considers you. You can't think of everything but try.
11.
Pack for Camping. Really thats what we do when we go out. Its just a matter of length of stay. One day? Three days? You need water, food, a way to cook, clothing for the weather(s), and a warm dry place to sleep. The trick is to not over/under pack.
12. Go Sailing.
I'm not going to tell you what you need - you need to tell you what you need. I only offer an approach.
Happy Sails