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It is certainly doable if:
1. you have the money;
2. you have the skills;
3. you have good health;
4. you manage to get away not when it is stormy;
5. you have a companion to watch your back;
6. you are certain that you can get to your craft before someone steals it.
7. I was curious so I looked up the cost of maintaining a 30 foot sailboat (and I don't know too many people who can operate it and maintain one alone). It worked out to 15% of the cost of the craft per year.

One day I was in a class taught by a Force Recon Marine. I was not a Marine. An older, overweight, middle aged guy with an SUV asked the relatively indigent Sgt. what he would do if shtf. He responded that he would find an overweight guy with an SUV, take it away from him and bug out with his girlfriend!

I had a friend, now deceased, who sailed frequently out of Los Angeles and had a lot of friends with sailboats. How could he do it as most times, he worked as a gardener. The answer was that sailing ships were always short crew members and he would sail for free and be fed. So, maybe you do it this way.

Here are two other ways of skinning the cat.
 

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I think you have figured it out. The first rule of survival is to be in the right place at the right time.

Now, let's explore the three main factors.

You travel a great distance on regular basis. Assume that shtf happens to you when you are in the travel mode. Your inquiry has been about equipment. So, what equipment do you available to you while you travel? Are you prepared to go to ground for a few days in place? It is not an idle question. I drive less than 200 miles a month. However, if I am out and about in the car, I am prepared to go to ground. My car is never more than 100 yards away at any time. A boat is worth nothing to you and neither are relatives 200 miles away.

If you think that you will be near a marina when shtf, then focus on making friends with a boat owner, learn how to steal a boat if necessary, and think about what you want to take with you.
A low income earning USMC Force Recon Marine was asked by an overweight white male who had money (and an offroad vehicle) what he would do. The response, collect up the guns and wife and steal an suv from a fat old white guy!

Let's speak to skills. Have you been an Eagle Scout, been a grunt in combat or paid for skills sets like hunting/tracking/small engine repair/shooting/fishing/swimming/cpr/Heimlich?

If you don't have those skills, understand that having a radio transmitter isn't going to help you. I have done disaster communications service as a volunteer. No one is going to come help you when shtf. I know you don't believe this, so ask around what your community has put into storage to keep you alive. Or, like my spending time trying to get roadside assistance when my transmission blew at night near Baker, CA- my communications gear did not help. My suggestion to go check out the boy scout merit badge manuals from the library and give yourself the challenge of meeting the requirements for a couple dozen merit badges.

Let's now address physical/mental health. I am old enough to be your father. I am not on any medications. However, I have an hour walking in the pool every day for a torn rotator cuff (had both shoulders done years ago) plus another hour of exercise (every day). I know a guy my age - 71- who was a world class athlete and still competes in seniors decathlons! It doesn't matter than I walked through the Khyber Pass from Afghanistan to Pakistan exactly 40 years ago.

You need to accurately gauge your physical capabilities. Moreover, you need to keep your shots/medical examinations/dental work up to date. If you wear glasses, do you have an extra pair in the car?
 
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