my problem is my current mental state is so low that a trip scares me without having someone to be the voice of reason
I believe the key word is "assisted" as in "psychedelic assisted therapy", it is advisable to have a psychotherapist to guide you through the path, I won't try to heal myself just by taking psychedelic (not the first few times, at least).
In this regard I would recommend reading Michael Pollan's "How to change your mind", the first chapters are a historical reconstruction of use (therapeutic and recreational) of psychedelics in western culture, from the 1950s to the present day. There's also a chapter on the author's experiences (with clandestine "guides") but the chapters that I found most interesting are "The Neuroscience: Your Brain on Psychedelics" and "The Trip Treatment: Psychedelics in Psychotherapy".
I found this book truly enlightening.
Just my 2 cents.
Forgive my english ;-)