>>42691976I personally would try to get a pokémon that can fight from the start (a rattata or similar), and train enough so I can get more pokémon (going with just one is not a good idea).
Then getting money by fighting trainers shouldn't be really hard, specially near towns (cities can be difficult to beat). That way I can try and get a decent living style.
Sleeping at first would be done in pokécenters, as they offer free healthcare and shelter (tipping the nurses and talking nice to them will probably allow you stay there without a problem anyways).
Considering many /vp/ users would be tp'ed there, finding friends and acquaintances will probably make you safer (wild pokémon can hurt you, people could try and steal from you, etc.).
Being the regional champion isn't in my to-do list, since it requires patience and dedication, but beating gym leaders can make your life "easier" due to the respect you will get.
That's what I can get from the top of my head.
