No, it's just very lucky runs. Once you get through the initial stage (requires some luck), it all boils down to whether you get elixirs regularly enough to keep yourself alive and whether you have that Divine Edge in your pocket when that dragon appears (so in the end you just want Pharmacies and Grim shops appear with 1 fight in between once you hit day 14 or so).
You'll need to unequip some of your dark defences sometimes though, to get Limit Breaks, such as Matt's cleaver, since Cosmic Monolyth heals itself almost fully every three turns, and you'll need a few lucky Airstrikes.
Beating the monoliths at 60 medals area is quite easy even on epic difficulty. The main problem is to get rid of ancient monolyth, and cosmic one is your best friend. Equip a set (Ninja Cloak, Swordbreaker, Pope Hat, Pope Dress, Obsidian, Officer's Hat, Officer's Coat, Shadow Blaster) so all your characters absorb dark, and rely on your evade (Guardian is best here when Lance learns it). Autolife status helps, so does Genesis. Use Fright to make Ancient Monolyth vulnerable to Doomsday which is cast by Cosmic Monolyth, and don't let it's evade get boosted. Once you get rid of Ancient Monolyth, the fight is pretty much won, since Cosmic Monolyth can only damage you with it's Flare-like attack before Doomsday, and his other attacks will heal you instead, and Viking Monolyth cannot dispel or heal.
It seems to be impossible for me to get Pirate Treasure medal. I've hit every wall at Rock Lake, checked out the walkthrough - all the chests are looted, but medal is not present.
Tselinoyarsk is the best farming city. There are only military and men in black (you get more money for killing these). Upgrade your Tank to max level, spawn it, grab your 15.000-20.000 every single attack. It's better to save up Tselinoyarsk for a while if you want to get "Mad Scientist" achievement.