Your dog has that soulful look of a rescued dog and I understand. My rescue
dog went to rest a couple years ago at the age of 13.
My 16 y/o boy asks about getting another dog - two years and he's off and I got 10-11 more years to care for a dog - nope. Past that stage. Too many issues with dogs
But this is about you. You are single
and work as a bartender and have the water
Pack your trash and go to Florida
. Get a $1,000/mo apartment there. I don't see anything keeping you in Missouri and in FL you can go kick a lot of tires - there happens to be a few boats there.
Bartenders seem like sociable folks for the most part - make some friends. Have them watch the dog for a week and go investigate jobs in the Caribbean
Ahhh. To be 32 again... I wish I knew then what I think I know now...