Q.Soil
How often would you put soil conditioner into the soil
I would start with a soil test to measure how your soil is doing. "Conditioner", not a well-defined term, usually isn't necessary. It is an expensive combination of fertilizers, minerals and organic matter. If you have nutrient deficiencies, you need fertilizer that addresses your particular problems. Recent research is pointing to benefits to soil structure from a 'don't dig" method for gardening, including incorporating soil amendments. Only dig enough to ease your plant in. Adding compost to the soil surface will improve the structure of your soil as soil conditioners claim to do. Here is more info: https://www.gardeningknowhow.com/garden-how-to/soil-fertilizers/what-is-soil-conditioner.htm