Hobo Dave's guidelines for transcending the grind.

• Using  a fresh, secondary character slot when you start is highly recommended.
• Turn off the HUD for more immersion.
• ​Set your spawn point to last location.
• Drop firearms and ammo when loading into lobby - melee weapons & Molotovs are okay (these can be found on the streets if you look hard enough)
• Refuse all job offers, missions and paid activities - it's a slippery slope back to the grind. Your primary income should be the good sport bonus (welfare). If you accidentally find yourself with lots of money, consider withdrawing it with your other character slot, or perhaps purchasing an expensive gold chain or set of expensive rims for your rust bucket.

• Criminal activity should be limited if possible. Stealing cash from pedestrians & shoplifting items from liquor stores is okay as a last resort. Full robberies should be done sparingly. (Same applies to Gang attacks.)
• Begging for money can be effective, but might annoy others. Use with caution.
• Hobo life has a much slower and relaxed pace. It's best to avoid simply stealing cars or requesting your personal vehicle. An RV from pegasus can be used instead for example, which  leaves a personal vehicle slot available for your bicycle. Go for a walk or take the train

• ​Property ownership should be as minimal as possible. Hobo Dave has 3 x low-end vehicle lockups around the map - each contains only a bicycle, and are located close to the rail network. 
• Kill/death ratio is a meaningless stat - it's a flawed lens for measuring your interaction with other players. Focus instead on being friendly, funny and creative. The number of friends you make is a far better measure of successful interaction. Explore, take pictures and make videos. There are still unexplained mysteries in San Andreas! 
• It's nice to play with other hobos - both human and NPC, but occasionally you must interact with regular, non enlightened folks. Use non intimidating actions to display your peaceful intent, perhaps even sending a peaceful message to say hello. If they're hostile you can run away, use passive mode, or simply see how many kills it takes for them to give up and turn peaceful.