Things to check:

1. Partition arrangement selected. You have to make sure to keep the same partition arrangement between uploads.
2. Partition arrangement selected. You have to make sure that the partition arrangement you have chose supports OTA uploads.
3. You have to reset the ESP8266 manually after your USB upload. You can only do an OTA update to a sketch that has booted in "run" mode, not "boot" mode.
4. You have the right IP address / hostname selected? (I don't know how that is handled in the Arduino IDE...)

Things to check:

1. Partition arrangement selected. You have to make sure to keep the same partition arrangement between uploads.
2. Partition arrangement selected. You have to make sure that the partition arrangement you have chose supports OTA uploads.
3. You have to reset the ESP8266 manually after your USB upload. You can only do an OTA update to a sketch that has booted in "run" mode, not "boot" mode.
4. You have the right IP address / hostname selected? (I don't know how that is handled in the Arduino IDE...)
5. You must upload an OTA-enabled sketch for OTA to continue working.