You said the 'bypass' valve is located under the master bath sink. What is the piping distance between the bypass valve and the shower?
A single shower head typically has a maximum flow rate of 2.5 GPM, but many have a lower flow rate. If you are immediately setting your shower temp control to where you usually find the temperature comfortable, depending on your usual desired water temperature, the hot water flow rate maybe significantly lower than 1 GPM.
Depending on the distance between the bypass valve and the shower, at less than 1 GPM, considerable time may be needed to clear the cold water from that section of hot water line.
Since most bypass valves stop hot water recirculation flow once the valves inlet water temperature is ~100°F, additional time will be needed for the hot water arriving to the shower to rise to the WH's maximum delivery temperature (usually 120°F max).
Suggest when preparing to shower, turn on the shower control fully to 100% hot until hot water exits the shower head, then reduce the flow rate and temperature as desired before entering the shower.