That Benevolent Leader trophy sounds like quite the pain in the ass. Not looking forward to it!
I was not too far behind him with the platinum, I tried to beat Greg but I got called into work and he beat me to top 50. The misc. objectives trophy is the real PITA.
For Benevolent Leader-
Final goal in the settlement is:
20 settlers.
Scrap all TVs.
14 settlers assigned to Tier 3 Surgical Clinics
Build a recruitment beacon or 2.
Build hundreds of paintings.
Put all beds indoors.
The rest of the settlers assigned as necessary to make sure food is high enough.
Defend with turrets.
Visit the settlement periodically. You will see an exclamation point in the pipboy on your settlement's happiness when someone in your settlement needs help. You must travel to the settlement and talk to everyone until you find the settler needing assistance. Finish helping and report to Preston if necessary.
Dismantling all TVs gets rid of the bug of happiness dropping. You do not need to stay in the settlement to keep happiness up.
It is going to take a long time to save money to buy so many clinics but this will 100% get you the trophy. You do not need anything else other than these things. You do not need defense of 400, power of 100+, etc. You only need just enough that everything is in the green.
Love the podcast btw!