If you are using much downward pressure on the razor as you strop you are doing a disservice to the razor's edge. Under normal circumstances your stropping motion should be should be light as a feather with the edge, while the spine is in constant contact with the strop, acting like a plane taking off and landing. You should hear almost nothing from the strop as you lap. Linen, or felt, or web material first, followed by leather by 'x' number of laps (it will vary based on feel for the strop, emotional state and level of OCD). Crox and diamond spray refreshing is usually after 15 or so shaves and to the barber's hone or 12k or higher stone after maybe 30 shaves. That is, if you have a "normal" beard. More or less depending on beard density, etc.