In the midst of resenting the amount of stuff we have in our house, I must have had a romantic vision of getting rid of everything and becoming a hobo. Given how unrealistic (and honestly, not all that romantic) the idea was, I had to do the next best thing: design a game!
Be warned: what follows is a brainstorm. Ideas within may contradict each other, or might not make any sense!
The heart of the game revolves around jumping on trains to hitch a ride to various towns to find jobs. Jobs provide money and/or food, change your reputation (positively or negatively) with the town and/or the hobo community, and change your happiness. Victory conditions are based around money, happiness, and reputation.
Food is required periodically, or else you'll lose some happiness.
Happiness is factored into your final score.
Money is required to buy food and train tickets. It also factors into your final score.
Train tickets allow you to legitimately travel on commuter trains. Otherwise, you have to jump a freight train.
Reputation allows you to get better jobs or receive charity. It also factors into your final score.
The board is a hex map that contains several towns. The towns are connected by railroads. If it's not too complex, some of the railroads may be commuter trains while others are freight trains. If it's too fiddly, we can pretend they are one in the same.
The trains move between towns autonomously. The train tracks would be segmented into spaces, and each space would be 2 (or 3) hexes in length. Each turn, every train moves one space. Hobos can board trains when the train is at the train station (otherwise the train is moving too fast!).
In a town you can take one of the jobs currently available there. Jobs may have a reputation requirement before you can take them. You can take charity in town, which provides money or food but hurts your reputation. You can use money to buy food in town.
Turns correspond to trains moving one space. Jobs may take multiple turns to complete. Hobos may move by foot one hex space each turn.
That is the basic framework I have in mind, but I already see a glaring problem: moving one space per turn, or waiting for a train to get to the next town, or waiting for a job to complete could be boring. Perhaps in practice it would move fast enough that it wouldn't be a problem.
The map might be the biggest challenge. Routes would have to be designed so that there are multiple ways to get around. Going by foot should be inefficient, but viable if a train isn't immediately available.
I can see this becoming more interesting as a design problem than as an actual game!