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Save up another 10k and get a ROAD KING.
Save up another 10k for all the knick knacks you wanna dump into it.
Coolest cruiser Harley makes right now, put some chrome 16" bars on there hell yeah brother.
Also being homeless and so exposed on a motorcycle is a terrible feeling knowing you don't have a room to go back to, I'd start with a van or truck...
You also need gas money, food, water, a few extra thousand for any tires or work you need to get done.
Road tripping is actually expensive as fuck if you haven't realized yet....