Hi there!
Your sentiments certainly resonate deeply with me, being a "20 year old wanderer" myself, and I sense that you are exhausted by those persistent cycles of skepticism. Although I am ignorant to the personal nuances comprising your situation, I understand the insipid fog that envelopes the mind and soul in such a constant flux of existential doubt; it leaves me feeling isolated and cold.
Whatever the case, your cognizant approach to psychedelics, particularly DMT, is mature and will lead you down exciting paths. DMT is undoubtedly a master in the shedding old perceptions - successfully reintegrating these altered perceptions into your "waking consciousness" and learning from them, however, is contingent on your effort. Tread lightly
-edit- I am still incredibly inexperienced with psychedelics, however. I have much growth and learning yet ahead of me...
"Tears themselves interest me greatly -- but not the tears of melancholy hindsight and existential despair;
rather the tears of awe you experience when the realization of an ideal suddenly appears before your very eyes or thunders inside your mind;
these tears interest me." - Philip Hallie