There's a guide or two floating around, to get the trophy you need to build a ton of shops as well as fill the bar and...just going to http://www.gamesas.com/topic/1574556-100-happiness-in-settlements/ for you...
One of my settlements seems to be poaching settlers from the others, greentop nursery has 29 settlers
mines kept complaining about beds even though I filled the whole dam place with beds, I had 4 times more beds than the whole population and they kept complaining. So I stopped giving a [censored] whether or not they are happy.
The glitch is it's bugged right now, so glitching it to make it work is all we got.
Personally I don't care, I don't chase achievements in games just to win a badge, rather just have fun playing and enjoy myself.
I got this trophy completely by accident in Starlight Drive In. I just wanted to build up an actual town, I wasn't even trophy hunting yet, but here was my set up:
I have 18 settlers there, just the standard "Settler" type, not any named NPCS. I have a BUNCH of shops there. Three level 3 Clinics, Two lvl 3 Clothing shops, three lvl 3 general traders, three lvl 3 restaurants and one each of level 2 armor, weapons and trader shops. I wanted a cap generator, but hey, bonus! it also gets you this trophy ...the town is built up around the "lake" at the middle of the drive in that somehow can support a huge water purifier. So there's 40 water coming in from that. Theres a bunk house that sleeps 14 comfortably under a solid roof (this seems important for happiness) and a few other buildings that house the rest of the beds. A decent size farm sits over by the workbench manned by 4 farmers, each tending an identical plot of 3 mutfruits, 3 tato plants and 3 corn plants (yay! adhesive!) for a total of 24 food. Turrets ring the outside of the town for a total of 64 defense.
As I was setting this all up, i noticed the happiness rising at a pretty decent clip. Once everyone was moved in and assigned to a shop (happiness was just under 90 at this point), i started working on some lightbox signs for the various shops and built myself a little mansion to store my stuff...i get pretty OCD about this stuff, so i was tinkering with all that for at least 3 in-game days. By that time, the happiness was at 97%. i figured at that point i may as well just get the trophy since i was so close, so i read some guides and learned that leaving is a bad idea as your happiness goes down. I hung out with the settlers for a few more days, having drinks at the bar and shopping at their stands, which got the % up to 99, but it just wouldnt turn over to 100...i figured I'd need another shop to turn it over (as per most of the guides) so i fast traveled to sanctuary to send someone from there to the drive in to run another shop. When i showed up in sanctuary, the trophy popped. *shrugs* ok, i wont argue!
So anyway, TL:DR - this is the setup that worked for me:
4 Farmers, each tending 3 mutfruit, 3 tato, 3 corn -- 24 food
40 water from a large purifier
Level 3 Shops - 3 clinic, 3 trader, 2 clothing, 3 restaurant
Level 2 Shops - 1 weapons, 1 armor, 1 trader
18 beds, all under solid roofs
64 defense from various turrets
I accidentally got it yesterday too, using no shops and only 1 settler (Deacon)
People are chasing it because it's a "rare" (about 0.7% of players have it).