I don't know the circumstances as to why 2/3rds of your sessions end feeling like you wasted your time, but those situations may have been preventable in some manner. This is the odd game where your entire experience is dictated by interaction with other players so yeah you can get in a pattern of losing and it feels bad.
- Hit the outpost often. Don't sail with an amount of treasure you are not willing to lose.
- Keep one eye on the horizon (even from on-island), spot other ships early and keep your eyes on what direction they're heading and communicate to your crew.
- Don't give an approaching ship enough rope to hang you with. If they don't reply to messages/call-outs on speaking trumpet, are flying the jolly roger/black sails (regardless of alliance flags), or are sailing a larger ship than your crew, assume aggression.
- If you have no treasure and are being chased, try to turn the tables - use it to get experience in PVP and if you lose think of some things you might've been able to do to prevent it.
- When a crew is overly aggressive toward you/sinks you, leave the game and switch servers.
Sometimes, you have to take the L. And it sucks, in part because as you mention you can end up with sessions where it doesn't feel like you accomplished anything. When that happens to me I take a deep breath, start a closed sloop, boot in and look for a shipwreck around whatever island I start on, I do that shipwreck (as 95% of the time you'll spawn out of view of any other player-controlled ship), cash in at the outpost and call it a night - ending on at least a little bit of a high note.
I have a million gold. I don't know how you'd price an item to be so expensive that'd prevent me from buying it and using it on you but being affordable to a casual player to prevent getting outplayed by an experienced crew. And same for collecting such an item in the world (though I do like those too).
