San Diego, California or Naples, Florida

Which is most becoming to the homeless lifestyle, assuming you do not do any drugs and absolutely will not seek government assistance?

My hobbies include
*Day trading on phone app
*Going to the gym
*Loitering at the library
*Loitering at colleges and sneaking into lectures
*Going hiking
*Riding my bicycle
*Stealth camping
*Doing odd jobs
*Doing jobs I think would be fun for temporary amounts of time

Previous location was Kentucky for two years, I survived the winter(some nights get into the negatives) and survived the summer(some extremely humid 100 degree days), I am now deciding that if I want to keep this up it would be much nicer to choose a location with less taxing weather. I will miss Kentucky, it is beautiful but some days the weather is so rough it gets in the way of clear thinking and leisure which are two very important things for me.