You don't get the achievements the moment you unlock them, you have to go to the Achievements page on the start menu and read the events to unlock the actual Steam achievements.

Professional Consultant
Achieve any ending
You’ll get this when you clear the evaluation 3 times, or when your Information level reaches 100% and you read the corresponding News event.


Super Consultant
Achieve an S rank
You need to get 8 points or more on the evaluation.


Dead Broke
Failure to pay rent
You should have less coins than required to pay rent at the end of the week. A tip is to buy expensive items at the start of the game, and then only focus on increasing Bubbles’ popularity to decrease revenue when you don't have any equipped items.


Incapable
Evaluation failure
You need to fail the evaluation. If you only focus on getting Information points, chat with the girls, and don’t equip them with any items, you should be able to fail the evaluation.


Secret of the Spirits
Pass the S route for all characters
Get all 3 character endings (requires S-rank). The easiest way to get a character ending is to just focus entirely on one girl the whole game.


Gratitude of a Cat
Feed wild cats at least 5 times
While playing the game normally, Special Events where you’re able to feed stray cats will appear. You need to choose to feed them 5 times for the achievement. Progress carries between playthroughs.


A Merchant Must Be Sly
Reach the lowest level of Reputation
You need to get the worst Reputation possible, which is “International Enemy”. Be as awful as you can and it should appear easily. Here are some ways you can lower your reputation:

• Accept offers to lower cost
  
• Don’t feed the stray cats
  
• Steal money from the wallet
  
• Accept offers to do bad deeds

While you're at it, you could also go for the "Do As You Wish" achievement by purchasing the Basic Employment Laws for 200,000g, since you need a low reputation to be able to buy it.


Billionaire
Gain the Upstart’s Collection
You need to buy the Upstart’s Collection from Items, it costs 9,999,999g. You should be able to reach that amount by playing through the game a few times and unlocking the items for finishing the girls’ S-rank routes, getting the training items and the Angel Necklace from reaching the 70% Information level. Equipping these items at the beginning of the game should be the boost you need.


Do As You Wish
Gain Basic Employment Law
You need to lower your Reputation to “Incarnation of Evil”, and then buy Basic Employment Laws from Items for 200,000g.


Cooking Duel
Lulu’s Quality surpasses 300
You need to get Lulu's Quality to 300 by studying cooking and reading her events. Items don’t count for the achievement. A tip is to focus on this while getting her S-rank ending.


Welfare Handout
Bubbles’ Popularity surpasses 400
You need to get Bubbles’ Popularity to 400 by doing flyer handouts and reading her events. Items don’t count for the achievement. A tip is to focus on this while getting her S-rank ending.


High Calorie Idol
Aurora’s Popularity surpasses 300
You need to get Aurora's Popularity to 300 by doing flyer handouts and reading her events. Items don’t count for the achievement. A tip is to focus on this while getting her S-rank ending, her lv 27 and lv 30 events give 120 Popularity points total.


Truth
Achieve the hidden ending
You get the hidden ending by getting the Information level to 100% and then reading the corresponding News event. You can only increase Information once a day. You can also buy information from Sakura to increase your level.


Food Girls
Achieve the perfect ending
The requirements is to get all girls to level 27, as well as get an SSS-rank (11 points at the evaluation). Here is a Steam guide for the achievement.