You have a marginal condition if you are trying to lift water 29 ft. You should have the following equipment to help diagnose pump problems:
Vacuum gauge (30" Hg to 60 psi) on the suction of the pump
The multimeter will let you determine if you have power at the pump. If power at the pump and no sound indicating turning of the motor, then the motor is shot or it has tripped its internal overload. If it's overload, it should come back on in minutes, unless it has a push-button overload reset.
Your pressure swtich may be set pretty high for a 1/2 HP pump and deep suction. If you can get the pump to start, you might try to run it with a discharge valve open until you establish flow. You also may want to reduce the START pressure on the switch to 20 or 25 psi, and set the tank air pressure at 2 psi less than the START pressure.
The vacuum gauge will tell you if the water level in the well is too low. One inch of Hg is 1.13 ft of water. If the vacuum is more than 22" Hg (25 ft of water) then you are at the limit of the pump. Zero vacuum on the gauge tells you that the pump isn't lifting anything.