calibre is designed to convert files from arbitrary sources that can be arbitrarily messed up. As such relying on files complying with the EPUB spec is very optimistic
There was a regression in 0.8.18 that made the set of guide entries that worked smaller than in 0.8.17. That has been fixed for 0.8.19.
Basically the (fixed) algorithm is that either title or type must be start (case independent) and the last entry wins in case of multiple matches.
And note that the entries that end up in the <guide> in the MOBI file are irrelevant. The new calibre MOBI engine (in 0.8.18) writes contentstart into the EXTH header, which is always used by the Kindle in preference to whatever is in <guide>.