Ok...The advice I'm about to give you is my personal opinion from personal experience, as well as being the "baby-sitter" and the dosage administrator for various psychedelics.
Tripping is all in the mind. Mainly your subconscious. Knowing what kind of person you are doesn't necessarily determine how your trip is going to be. But it can determine whether it's going to be a good trip or a bad trip. If you stress and worry and muster up all these different scenarios that could happen, that can have a lot to do with the direction this trip is going to go. Regardless of what kind of substance you decide to do, just know that it's going to be an enlightening experience. As long as you pay attention and learn from what it has to teach you. Even if it does turn out to be a bad trip, there's still something to learn from it. Even if it's just finding out that your mind wasn't strong enough to handle it. I believe that as long as you're not scared, it will be a pleasant experience. You already seem like you're ready for the experience and curious as to what you will experience. I myself have done MASSIVE amounts of shrooms, LSD, DMT, Ketamine (and yes Ketamine is a psychedelic trip) and I'm sure there are some other substances that I've done that I can't remember. I've only had 1 bad trip and that was because I convinced myself that the acid I took was mixed with something else. Which it wasn't and I freaked out for a minute, but I was and still am fine. I wouldn't say that DMT is a more powerful psychedelic than shrooms or LSD, but it is definitely different. Much more personally insightful. If you'd rather do DMT because of its short duration, go for it. Just realize that you're diving into a much more self reflecting experience than LSD. In my experience, LSD and shrooms are also self reflection but, for me, it's almost like putting my mind in someone else's body. It most certainly gives you a very different perspective of perception. You know the saying "Two minds are better than one" that's probably why a lot of people come up with some out-of-the-box, but very good ideas. Hell, Bill Gates designed windows will tripping balls on LSD. Anyways I can sit here and type and type about this stuff so I'm gonna shut up and leave it at that. If you have any other questions, feel free.