Truth is, there is no reliable data regarding how bad is the effect of transcoding on quality. A test was
attempted once transcoding to --preset medium from different sources, but for some reason it didn't get enough participation to get statistically valid results and therefore was indefinitely suspended. Too bad, since I do think it would be worthwhile to know for sure just how much of its terrible reputation is real and how much is myth.
I tested several samples in the test and even though I never found out what my results were, there were always one or two codecs that I couldn't ABX from the direct transcode. The strongest candidates in that test were WavPack lossy and MPC insane, so I guess it was probably them as sources which I couldn't ABX. I don't claim to have exceptional hearing nor equipment, but I wouldn't say I am any less than average, and if I couldn't ABX some transcodes, then they can't be so bad. I heard kinda extraofficially from Steve (sthayashi) that in his insufficient and preliminary results MPC insane was standing pretty good.