It should, but it doesn't always. I had a few rips that didn't work well and crashed the PSIO in a way that I had to re-do the initial setup. May also have been a/the problem with SD card reading that was previously worked around by using 1024 KiB allocation size instead of the 256 KiB suggested by the manual.
Other than that, it's just an easy way to make sure that that the image really should work, and if it doesn't the problem is likely to lie on the PSIO side of things.
You probably know this, but in case you or anyone else reading this don't: Redump is a database which lists the checksums for virtually any (PlayStation) game, which can be used to verify that the file one has on their computer is absolutely identical to what other people did read off an original disc via a controlled, elaborate method - eliminating or reproducing read errors (some copy protections).
My theory is that images from the mostly cheaper drives that are used today are likely often still good enough, but offset isn't taken into account when ripping and thus, hashes mismatch those from Redump. I want play around with that theory at some point, but haven't had the time yet. If I'm right, those images should still work, regardless of the offset (which is like a few seconds at most).
To check if a game is Redump
You can get checksums (MD5, et cetera) with this command line tool from Microsoft
if you are using Windows. On Linux/Mac, you can use md5sum or md5 on the command line. Then simply compare the result to the hashes listed on Redump. Be aware that they, for whatever reason, don't list the hash for the single bin image, so if the game uses multiple tracks, you'd have to calculate the hashes before merging via Systems Console or any other means.