The motor usually has a "start" nameplate on it somewhere. The wording typically goes something like this:
"With rated voltage and frequency - within NEMA limits - at motor terminals and with connected load
inertia not exceeding value shown below, the following starting duty should not be exceeded.
Load inertia = NNN lb.ft2
Motor COLD = XX consecutive starts
Motor HOT = YY consecutive starts
Subsequent starts with motor running between starts = AAA minutes
Subsequent starts with motor standing between starts = BBB minutes
Starts should not average more than DDD per day throughout the life of the motor"
A "cold" start means that everything in the motor (e.g., all the steel AND all the copper) is at the prevailing ambient temperature. If anything is warmer than ambient, the attempt is a "hot" one. This is why the allowable number of successive starts for the "cold" condition (e.g., XX) is higher than for hot (e.g., YY).
The second part of the plate refers to the dwell time between one series of starts and the next. The duration for the motor "running" (e.g., AAA) is lower than for "standing" (e.g., BBB) because the combination of convection and radiation provides better heat transfer than radiation alone. Note that to meet the "running" condition requires that the rotor remain spinning at a significant percentage of rated speed for the entire duration.
As to applying a delay between the a "start" command and the next "stop" command: that is an excellent idea. If the start sequence was successful, the setting should correspond to the value listed for "motor running between starts". If the start sequence was unsuccessful, the setting should correspond to whichever condition applies (i.e., "motor running" or "motor standing").
Lastly - in certain instances, it may be advantageous to try to reclose the breaker or contactor "on the fly" while the rotor is still spinning. Some machine types can do this easier than others - in particular, the constraint for a synchronous machine is different than for a squirrel cage induction. It is usually better (for the life of the machine) to allow it to come to a stop before attempting to restart. How long this takes is dependent on the mechanical characteristics of the system (friction, inertia, the ability to "decouple" components, etc.).
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