To make the homeless-man-life TRULY feel authentic, burn your house down with all your stuff inside, then quit your job, assuming of course that in the time period that you go for this feat you have a job, then go bum around your nearest city park.
Oh, and my #1 thing is to rule the world.
Bucket list:
#1 Rule the world
#2 Live forever
#3 Toss out this stupid list