The big break (for me) in configuring the options was the very welcome addition of "make menuconfig" to replace the original "make config". As the number of supported filesystems/drivers/options increased, it could take more than an hour to get through a "make config".

I haven't built my own kernel for more than 15 years, but I probably built more than a dozen before that, each of them re-compiled upon every new release (going back to 0.98).