Ok this is where I'm at so far with matching up the clues:
Dota - Kaléko (2020)
Clue #1: [not sure how pagliacci's vesti la giubba relates to this]
Clue #2: [not sure how barry manilow's "mandy"]
Clue #3: no idea how the knack's "my sharona" relates
Clue #4: no idea who this guy is
Clue #5: dancing doctors?
Clue #6: not sure about the Ellis & Tom connection
Clue #7: I think the label is based in Kreuzberg - I found this address on the label's website: Wrangelstr. 84, 10997 Berlin - which appears to be in Kreuzberg
Clue #8: Album is sung entirely in German
Clue #9: That logo appears on the back of the album but I can't find it anywhere else on the internet. The label is Kleingeldprinzessin, and I don't see it on the label's website, but maybe I'm missing something haha
Clue #10: Mascha Kaléko was a German poet and all of the lyrics on this album are credited to her!
Clue #11: Discogs lists 3 variants: 1 LP release and 2 CD releases
Clue #12: The last image is Chemjo Vinaver, who was married to Mascha Kaléko.
I've been listening to it and it's really interesting. Some of the songs are kind of playful and some are more somber, but Dota Kehr's voice is really nice and she collaborated with a lot of talented musicians and singers. Great pick, Jan!