Hi. Welcome to Just Answer. Try pressing the button on the unit first (the learn button). Program the wall unit first and then the remotes. If that does not work try programming the remotes and then the wall unit.
If that also fails then you have the "Sears syndrome". For some reason the Sears units have a bad habit of blowing out their programming and not allowing the remotes to be reprogrammed. All it will allow is one sending unit to be programmed and will not allow multiples again.
Unfortunately this is an error in the main control unit and in the end it is just cheaper to get a new unit all together.
Hopefully one of the programming methods will get you back up and running. If not I am sorry but replacing the unit is best.
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I'm in a rental house, so replacing is not an option. Are you able to send over a detailed explanation-- step-by-step-- of how to best accomplish this? Assume that you're working with someone who sucks at this type of project :-)
This is what you posted as already tried:
"1. Press remote button 2. Press orange "learn" button on back of opener, wait until it flashes 3. Release both remote and orange button"
All you need to do is reverse the button pushing.
1)Press and hold the "learn" button until the light starts to flash. Keep it pressed and press the button on the remote or have someone else press the keyless entry unit.
2) once the button has been pressed release the remote button and then the learn button.
That should program the remotes for you.
If it doesnt work try releasing the learn button after the light flashes and then press the remote button.
If both methods fail the main control board will have to be replaced.