This all seems to be behaving as intended now after patch 5.71.
Can happily say all my settlements had requests, either building requests or disputes. After completing them I got that nice timer indicating they are preparing the next proposition. Knowing I had twenty minutes I found small buildings in need of upgrades and set them to do that while the pop prepares their elevator pitch.
Did this for all three of my settlements, left feeling contented. But Iām seeing what you were all talking about now, with trade market items being a big requirement for the a/S class building upgrades.
Which reminded me, of a feature I totally forgot about, doing a trade station scan in space now gives the option to scan for local trade deals, pointing you in the direction of some cheaper than usual trade items.
Iāve decided Iām gonna let that be my guide instead of looking through rows and columns of what product is found in what industry type etc.
Like a leaf on the wind ( * has serenity flashbacks* )
I have a Vykeen settlement I started during worlds part 2, which replaced my original settlement.
I now also have an Autophage settlement. I got this after accepting the guided mission version that arrives to an existing settlement overseer, quitting that post immediately because native australiafied weather and fauna. I used a autophage chart to find one on a waterless Titan planet that I thought could use a fishing hole 
My third and newest settlement is a Gek settlement in a redacted planet.
When I arrived it was empty, nobody walking around, not a gek in sight. The weathered wood really sold the ghost town on a western frontier vibe.
Becoming overseer and building the office suddenly made the populace appear and immediately a Gek came marching out of the office.
Im not sure if this is how itās supposed to happen but I quite enjoyed it, all it was missing was some tumbleweeds
Just need a Korvax settlement now 
Oh and dear Hello Games, please add geometry to this so I can sit and hang out with this Autophage