Buy a beat up 27, get moorage in the city, and live aboard. This will probably cost you at least $3000 to start and $500 a month. Then you will need to get a job. This is easy if you aren't picky... You will probably be destitute, but you will get to enjoy life on the water. That's about what I am doing. Just remember, just because it isn't conventional doesn't mean it isn't good.
Don't get steamrolled by norms. You don't have to live in a house and pay a mortgage. In fact, living on a boat can save you a lot of money which you can use later to buy a house or whatever.
We are all born