For the first ten years of my psychedelic use, I took them once or twice a year at most, sometimes skipping a year or so. This didn't include salvia divinorum, which I used much more frequently for a few years. After a spell of depression that lasted more than half a decade where I took very psychedelics, I decided to throw caution to the wind. Realizing that the depression had done more harm to my mental function than drugs ever did, I returned to psychedelics and started using them once every week or two for several years. Over a period of months, my depression started to recede and has been mostly at bay provided that I take a psychedelic once every two to eight weeks, with efficacy dependent on the psychedelic, the dose, and the duration. Some work well, some do nothing at all. They have definitely played a huge part in bringing joy and satisfaction back to my life, and in helping me get out of ruts and form healthier habits and relationships over the last five years. I find that I don't need to use psychedelics all that frequently anymore now, in part because of the benefits they've imparted already and in part because there's less guesswork in finding out which will be beneficial.
Because of my better understanding of these materials, I use them more like specialty tools. It's hard to say how often I "trip," because I use them so differently. I might have one proper psychedelic experience every 4-6 weeks, but I might intersperse some low dose use of short acting phenethylamines to enhance a visit to a concert or art gallery. Similarly, I might vape a strong dose of a light, short-acting tryptamine after work here and there to kick myself out of a bad mood or spend some quality time with my partner. Neither of these fulfill what I'm looking for out of a typical psychedelic experience, but improve my quality of life in much the way that I feel others use alcohol, but healthier and more targeted. It's nice to have extra tools in the toolbox.