Don't give up, stay motivated, and be creative and proactive... No matter what you want to do - that will get you there. It's usually people who give up OR pursue halfheartedly that don't achieve their goals.
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Well my perfect situation would be playing at small events, like weddings, reunions etc...
Is that achievable, with a somewhat decent revenue?
Have I given my standard speech yet? In brief: I make a good living playing music. I just finished doing seven 5 hour gigs in the last 8 days. In a nutshell, here's my advice:
A) You have to go to where gigs are. Not necessarily NY or LA, but a major city. Wedding/function bands make very different amounts of money depending on where you are. Research those markets and figure out where the money is.
B) Learn A LOT of songs. Jam in E is not a song. There are hundreds of songs to learn that are standard repertoire. Get started now.
C) Develop other money- making skills besides bass. I play electric and acoustic, ceremony guitar, ukulele, do PA, DJ, I'm the booking agent and bandleader and most importantly...this is the biggest thing I can tell you...in my mind this the entire tweak to whether or not I can make a living playing music... I sing. Lead and backgrounds.
LEARN TO SING, LEARN TO SING, LEARN TO SING, LEARN TO SING, LEARN TO SING, LEARN TO SING, LEARN TO SING.
A decent bass player who sings is worth 20 times as much as an amazing bass player who doesn't.