>>2281152>>2281203>>2281352Just fuckin send it. I'm a shitty eternal procrastinator constantly crippled by anxiety about what ifs and managed to do it by summoning the big retard energy and just pulling the trigger.
Obviously don't waltz into it wholly unprepared but once you're reasonably prepared for like 75-85%% of the foreseeable issues just get yourself all riled up and do it. You'll never be 100% ready because there's always some little stupid thing that needs done or could be better or some stupid niggling little what if.
I've had cruisers and boat bums alike tell me that if you wait for perfect you'll never go sailing.
Also the scruffiness of living aboard helps filter out bad matches real quick.
I lived for 4 years on a 30 ft sailboat at anchor with a lovely woman and a cat. We bathed in the sea, we shit in a bucket and we were happy.