With all due respect I think there is a paradigm of the "average" cruiser that might need to be blown up.
We have 3 X 20 year old guys with a sense of adventure. At 20 you can make
mistakes, endure hardship and suffer greatly while thinking you are having fun...
The link to the boat above at $19k was a good one. Overanalyzing and over preparing is a big risk that could dash the dream: Here are some swing thoughts:
Buying and Selling the Boat - Go with the mentality that 50% of the boat cost is sunk and won't be recovered.
Buying is easy - selling is hard. Buy a boat for $18k with the expectation you will unload it for $9k. That should make getting rid of it easier. Talk to the
broker. Maybe he would like that deal and handle it all for you. If he
sold the boat for $12k let him keep the difference. Be creative.
The dink - Healthy young
men have lot's of options. We have swum to shore. We have used kayaks. There are options that don't require $20k worth of
dinghy.
Provisioning - Peanut butter and jelly. Instant noodles, mac and cheese. I've lived on worse diets.
Beer? hey if the
money runs out you go home earlier. Let's say you only made 3-months. It would be a cool 3-months.
Maintenance - If none of you have mechanical skills i think this is the biggest risk. Things break, things deteriorate. If you rely on someone else fixing them you can burn up your budget in a few weeks. I don't agree with the outboard. An inboard diesel is a very reliable item. If you have mechanical skills you should be able to figure out is the
engine is running well. We motored our boat for 2 hours at high speed as part of the sea trial. Do not be convinced to just use the donk to get out for a sail during your baot evaluation.
The right team? - If you don't have a mechanical guy maybe you invite a 4th who does have mech skills. Who
sails, who cooks etc, etc.
Bottom line is don't overanalyze it. Get out there.