First off; with writting this please understand i have a certain perspective on tripping. please take your own perspective into your consideration; no one has a "right" or "wrong" way to experience psychedelics.
I strongly agree with the second line; i always feel like tripping is sacred and special. So i don't like for it to be "just tripping" because honestly: when i'm "tripping balls" it's just not that simple! my Mood and Perception is just completely "drunk" off it's Serotonin supply (or the receptor is being "fucked with" by Psychedelic Chemicals in a less professional way of putting it perhaps), color and texture is like; different. it's all hard to put into words to be honest; at least a few words.
thoughts and "normalcy" are different; probably due to Serotonin Alteration which changes how i perceive and process information and stimulus. I realize i think much more Atypically and Imaginatively and Atypical thought is more profoundly understood; furthermore so is typical thinking affected and altered; sometimes i can think atypically and neuro-typically at the same time. Plus i have special needs through Autism, Bipolar, And ADHD; which means that the person i'm being sat by should understand how psychedelics affect my Spectrums of mental phenomena's/"Disorders" so to speak; basically they have to get to know me first hand and understand both my Atypical and "neuro-typical" thought process.
that's another thing i want to add; it would be seriously helpful and detrimental to prepare and integrate through intense, committed psychotherapy: where you get to know the individual who is going to be using the specified Psychedelic Drug as much as possible for a length of at least One to Three Months; if not a full year or two for truly serious candidates (a good trip sitter is someone who already meets this criteria; someone you seriously trust: another good candidate would be a therapist of some kind who understands you and has a bond of trust with you). Three months sounds like a long wait; but it is harm reductive to your experience. an experience will be much easier to handle, predict, and understand with more knowledge and relationship involvement with the individuals involved within the experience.
You should also understand that reading trip reports isn't the best way to prepare imo; it is an important process. a person should take at least a month or more to research trip reports of the specified drug. This by no means tells you how it will effect you; but it does give you a foothold into the experience; both crisis situation ("bad" trip) and heavenly experience; or more professionally "it gives you a foothold into different spectrum's of Psychedelic Experiences"; key word - Spectrum. i love that word.
Another thing i want to talk about is the importance of Set and Setting. We'll start with debate-ably the initially important factor; Set
Set:Set Refers to The individual; perhaps the "plot" of the "play"; or just the fundamentals of what makes up the experience through the individuals perspective. set is very important in understanding how a Psychedelic Drug will affect a person. Set can include Physical, Emotional, Social, and Behavioral Factors:
Set is You. It is your preconceived ideas and bias's and perspectives and viewpoints. it's your metabolism, body weight, height, and physical, emotional, and mental activity. set is also your psychology; which when we get into psychology and psychedelics it really gets interesting.
Set is important to think about during your preparation; which is pretty much a part of your set.
In my opinion if you have a healthy body, mind, and emotional life; you have a "good" set going for you. if you don't excersize healthfully with a balanced nutritional diet, have an unhealthy mindset and perspective about your situation, and have little emotional contact: you don't have a "good" set going for you IME; at the same time it's also dependant on your setting as well.
then there's setting which deals with environmental factors; like "who are you with?" "what is your relationship with that person?" "where are you?" "what is your relationship with your surroundings?" "are you engaged in activities? or just sitting quietly meditating or something?" "how long are you staying in a specified place? will you be moving around?". stuff like that.
set and setting are important to think about for the specific plan you have.(if you have a plan; some people don't take it so seriously; personally i'm trying to take it more seriously to see how it effects my trips but that's a part of my set; specifically a part of my intentions and preconcieved ideal of tripping)
i think that when you understand tripping itself, psychology, constructive psychedelic use, and destructive psychedelic use: you can essentially understand the way a person might have a difficult experience versus a posative one. furthermore you might understand that difficult doesn't always mean "bad" and easy doesn't always mean "good".
I think each person should have their own view point and perspective and approach to tripping; much like the different approaches to psychology. as you get to know yourself as a "trip sitter" i think you'll soon be more comfortable and confident: which i think is important.
not only is it important to make the tripper feel comfortable; you have to feel comfortable too. otherwise that can affect the people around you: including your tripper that you're sitting for.
all in all; everyone has their own way: my way is to prepare, integrate, and transform and take extra time to focus on the process and seriousness of preparing, integrating, and transforming through the use of psychedelics. but by all means: that doesn't mean tripping can't also be fun, enjoyeable, recreational, medical, theraputic, or difficult. it can be a little bit of everything in my experience.
I think Trip sitting should be a sub-psychology interest: just because there are many approaches and perspectives to look at it from.
OH and i guess my last bit of advice would to try keeping a trip sitter's journal; they can help out alot as you go along.