I thought I was just asking for a book, but Interlibrary Loan brought two gigantic folio volumes to my office this week, Wolfgang Harms and Michael Schilling's commented edition of broadside prints from the Wickiana collection in Zürich (thank you, Berkeley).
And immediately a whole new set of Toledo Letters show up. In vol. 2, pp. 314-15 and 334-35 (VII, 156 and 166 for the entire series), two broadsides are reproduced in facsimile that turn out to contain the Scandinavian version of the Toledo Letter (see Mentgen, Astrologie und Öffentlichkeit 111), printed in Augsburg in 1585 and 1585. The footnotes point to further editions, including a translation into Czech. (To my knowledge, broadside prints are not indexed in VD16, unfortunately, or at least not uniformly, so that these broadsides have no VD16 entry.)
These broadsides attribute the prognostication to Johannes Doleta, whose name was already familiar to me. Two editions combine Doleta's prognostication with that of Wilhelm de Friess, while others stylize Doleta as the "Pilgrim Ruth, hidden in the forest," recycling the woodland prophetic identity created a century earlier by and for Johannes Lichtenberger. There are at least five editions of Doleta's prophecy in booklet form known from the years 1586-88 (VD16 ZV 4633 and ZV 22756, as well as two others not recorded in VD16, and one Dutch edition,TB 4427). The Utrecht pamphlets collection has a digital facsimile of one of the unrecorded editions here.
And now it turns out that Doleta is none other than "Johannes of Toledo," at least in a very late and highly modified version (the pamphlets add a foreword and prognostications for the years 1587-1588 and other material that is not part of the older Toledo Letter). So now it appears that the Toledo Letter really did enjoy renewed popular interest in the 1580s with at least 5 pamphlets and 4 broadside editions, and appeared at least once more in the 1620s. Not bad for a prophecy that was already 400 years old.