What is the shortest meaningful run_duration you got to work for deep sleep? Any tips to improve?

Just one little hint:
The Wemos D1 mini already contains an internal voltage divider with 220k and 100k behind its A0 pin. If you want to increase the max input voltage you can do that with a single resistor in front of the A0 pin. This adds to the 220k resistor. In your case (4:1 divider for voltages up to 5V) you would simply put 180k in front of A0, so your resulting voltage divider would be (180k+220k) : 100k = 4 : 1.

With your circuit you will actually not get a 4:1 divider because the internal sum of 320k lies in parallel to your 110k and pulls it down more than you expected.