Reddit reviews Buy, Outfit, Sail: How To Inexpensively and Safely Buy, Outfit, and Sail a Small Vessel Around the World

Cap'n Fatty has at least one book that addresses this question. He would add a #4 to your list, "You live frugally while at sea." But he also mentions a pretty good list of "jobs you can do at sea" - including skills in demand among other boat folks. He even mentions a dentist who had an exam chair in one of the cabins on his boat, IIRC.

I'm sure you already are but if not, start keeping eyes on the local used boat market. Wait and watch then pick your pitch. If it's too good to be true, it probably is BUT there are motivated sellers. People buy 2nd boats before selling their current one all the time, people inherit boats they can't afford upkeep on, people leave them at boat yards. This is especially true for smaller and older boats where the annual storage and upkeep can exceed the value of the boat itself.

Set up a separate bank account and figure out your annual cost of ownership. Start getting used to setting that money aside automatically each month. It'll give you a head start on your sinking fund so any early upgrades or repairs don't sting as much.

I watched and saved for 3 years until I was able to make a late-season steal on a well cared for Cal 2-25. Owner bought it for 6k, was paying 3500 for a slip and 1600 for winter storage. He was asking 5k but I waited until late in the season and offered 3400 pointing out the fact that he's breaking even on asking price by avoiding the looking winter storage. We settled on 3800 and we took ownership with 2+ months of the sailing season left.

While you're preparing, read the following books:

• Buy, Outfit, Sail: How To Inexpensively and Safely Buy, Outfit, and Sail a Small Vessel Around the World https://www.amazon.com/dp/1456310038/ref=cm_sw_r_cp_apa_Hi8YzbQ3KFZYY
  
• Don Casey's Complete Illustrated Sailboat Maintenance Manual: Including Inspecting the Aging Sailboat, Sailboat Hull and Deck Repair, Sailboat Refinishing, Sailbo (International Marine-RMP) https://www.amazon.com/dp/0071462848/ref=cm_sw_r_cp_apa_lj8YzbYPNZDPR

oh..shameless plug for one of my heroes.

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https://www.amazon.com/Buy-Outfit-Sail-Inexpensively-Safely/dp/1456310038/ref=sr_1_1?ie=UTF8&qid=1537972806&sr=8-1&keywords=goodlander