Let me take a stab at your question. It's a question of watermark (Wasserzeichen) and type of paper. The pricey stamps on the upper left page (Michel Numbers 29-33) are for mint not hinged (two asterisks). They are identical to Michel Numbers 18-28
except they are on granite (gefasertes) paper.
Granite Paper

They have watermark 2.The 1957 issues below them (34-41) are also on granite paper but have a
different watermark, a number 3.
DDR Watermarks

The 1956 issues on the right are a different series, "Dienstmarken B" the other ones are "Dienstmarken A" The pricy ones there are for used (circle with a dot) or on cover (The little envelope). Most used issues encountered are CTO, Cancelled to order (filled circle). The only good way to differentiate between a CTO and a real used stamp is to have it examined by an expert.
DDR Officials can be confusing. I hope I didn't muddy the water.
Dan
