The timeout error can mean communication is not established with the microcontroller in bootloader mode.
The EA pin should have a pullup resistor ( say 10k ), to 5 volts.
The PSEN pin needs to be grounded at reset to enter bootloader mode.
(To run the program after it is loaded, PSEN is floating or high at reset).
If using RS232, it has to be converted from RS232 to TTL levels.
In Flip, the RS232 setup utility has to be run each time the microcontroller is reset into bootloader mode, before the chip is programmed, or it will give the timeout error.
Flip has to be showing the Signature Bytes, Device ID, etc. to show communication has been established.
Of course, the right device has to have been selected under the device tab.
In the RS232 setup, the maximum baud rate I can use is 57600, so lower baud rates can be tried to see what works.
The correct com port needs to be selected in RS232 setup.
If none of the above help, you might want to post the schematic of the setup you are using.