With all the handwringing SN talk from some experts of people putting to sea with limited experience, requiring CG rescue I would have thought this would be the ideal time to help and steer this gentleman into a safe course where he wouldn't require a CG recue. Especially with all the concern stated here to prevent further incidents from occurring. But alas we get a pissing over the rail lesson from one of the chief critics. Here's your chance to help vs. sensationalize and criticize with your expertise and critical advice.
Congrats on your new boat Sully75,
You certainly have a great goal to look forward toward and I applaud you that you are taking a measured open minded approach toward it.
I would get as much sailing experience as you can. Maybe at time taking more experienced sailors with keelboats with you to sponge off of or get other opinions.
I would avail myself of an offshore course lasting two days. Many of the lessons are invaluable and even the most experienced sailor can learn something from them
I would start with a list of things you should have on board, spare repairable items for the engine, sails and some of the important systems. I would have backups of paper charts and few electronic charts. I would have enough emergency equipment on board to save your life should something catastrophic go wrong until help could arrive, In your case because its cold water maybe an immersion suit etc.
I would practice emergency procedures so they are routine and not done for the very first time live.
I a sure other helpful people will chime in here to help you be successful on your venture. Good luck
I would make a list skills you feel you need to learn he should learn,
Then start working on both lists