There seems to be some confusion as to what will cause this to pop. Some places come with things built in, others don't. So this is exactly what I did...
I did not build at the ranger station.
I did not build at the church.
I went straight from the church to the warehouse. (Nowhere else in between.)
-Storage (fixed built-in)
-Bedroom (fixed built-in)
-Workshop (fixed built-in)
-Watchtower (did not upgrade)
-Medical upgraded to infirmary
-Sleeping area upgraded to bunkhouse
-Training area
-Library
-Storage (a second one)
After the warehouse, I went to the fairgrounds. (Again, nowhere else.)
-Fixed the facilities that were there
-Kitchen (already there)
-Dining area (already there)
-Storage (already there)
-Watchtower (already there)
Then I built:
-Sleeping area
-Sleeping area upgraded to bunkhouse
-Medical upgraded to infirmary
-Workshop (not upgraded)
-A second medical because I messed up, then tore it down and built...
-Storage, but I was trying to get this achievement, so I tore that down and built...
-Garden
As soon as the garden finished, POP!
Note, I did NOT build my own kitchen or dining area. The ones I had were built-in. I don't think that upgrades matter for the achievement.
I hope this makes things more clear.