If you dream of being a tramp, then such dream symbolizes the lack of freedom you are suffering from. Maybe you have to many responsibilities and work to do therefore you feel you need to get escaped. On the other hand, the dream could indicate your immaturity to take care of what belongs to you.

(See Destitute | Hobo)

…I believe there are people who dream the same dreams repeatedly, even down to the most minor details. One of the dreams I am continually dreaming is as follows: I am walking along the sea-front of some popular watering-place, which, judging by the style of houses and appearance of the people, I should say was abroad. The sun is shining, the sea exquisitely blue; whilst, to enhance the beauty of nature, a band is playing, and playing remarkably well, some gay operatic music. What I see, what I feel, what I think, has about it nothing of the unmistakeable idiosyncrasy of a dream, but all is rigorously self -consistent. I am enjoying myself to the utmost, when, on turning round, I perceive behind me a tramp — a man with a shock head of red hair, and features that are ineffaceably stamped on my memory. He is a blight,…

(Loafing | Loitering | Tramp | Vagabond) Seeing a destitute or seeing oneself as a destitute in a dream connotes a painful poverty, a self-damaging condition, ingratitude or disbelief.

…(Bummer | Cadger | Homeless | Tramp | Wastrel) A hobo wandering in the streets, collecting refuse and litters from garbage cans and rubbish in a dream represents someone who accumulates both lawful and unlawful earnings, or someone who divulges or exposes people’s secrets, or launders their private lives, or someone who does not mind his own business and asks questions that are of no concern to him. (Also see Beggar | Poverty)…

…To dream of an actor or actress portends success in courtship; an author, a rencontre with an old friend; a baker, missing a train; a builder, a present in the way of dress; a clergyman, neuralgia or biliousness; a coachman, an injury to the head; a chemist, getting into debt; a dentist, ill-ness or death; a dressmaker, kisses; a doctor, danger from cows and horses; a gardener, an accident to the feet or legs; a grocer, sickness; a lawyer, pecuniary losses and danger from dog-bites; a manicurist, presents from a lover, success in courtship; a parvenu, danger from tramps; a publisher, danger from stinging; a member of Parliament, a birth; a sailor, an accident to a clock or watch; a soldier, breaking china or glass; a tailor, quarrel with parents-in-law; a tinker, visit from mother-in-law, or debts incurred by wife or sweetheart; a tramp, present of a dog or…