It'd probably be a good idea to use the Dirty Pre-War Businesswear as well as it adds +5 to Speech.
Naughty Nightware is +10 and Button's Wig is +10 Speech, plus CHR. I also drink booze, and pop a Grape Mentats.
However, if you Speech skill is 60+ you get 100% Success. I got the trophy with no problems, but had a little scare. As I was winning speeches, the trophy never came. So, I knew I must have had 50 won by now and looked. 67! I thought, "Damn! Another glitch?" "Maybe I have to wait awhile after getting out of the convo... *DING* and there it was.
However, I won the Mayor McGrady speech to get it and screwed myself out of the Rescue From Paradise trophy. I load all the way back to Tenpenny tower to go back to the start and do it all over again. But, I got Strictly Business at the same time, so it wasn't that big of a deal.
Currently, I'm at Raven Rock going to meet the President, and only have that quest and one more to finish the game. However, I have several side quests to complete. I hope I didn't play to far and screw myself up again, like with the two trophies I mentioned above.
I need 10 more Bobbleheads and kill 3 more behemoth to finish out these trophies. Then, it's Agatha's Song and Shoot Head quests along with the two main quest trophies and I'm done with this game.
Some other stuff I've noticed:
* In taking advantage of the Bethesda Offices East Big Guns skill book exploit after collecting the 1st 4 books, waiting 3 days in between, I've now had to wait upwards of 5-8 days to get the Raiders to respawn. Is it better to fast travel back to Megaton maybe?
Only with a bunch of full conditioned Flamers. I wait three days, then four. You gotta wait an entire week for the enemy to respawn twice. Once after three days, then four. Repeat.
* Since I've added the Better Criticals perk I've noticed that it seems to have turned off the graphical effects of the Bloody Mess perk. Anyone else experience this?
I never got the Bloody Mess perk, but blood, eyes and heads go flying all over the place, anyway. Not always, but a lot of the times. Especially at 'Sneak Critical Shots' but I'm not sure if that's BM perk or not.