You will be able to obtain both a profession ending and a romance ending in one playthrough if you level your traits properly and utilize some clever save file loading.
**For demonstration purposes I will be using the Lora / Dancer path

• Set game to EASY. This will give you 999 days with which to obtain your desired ending or endings. It will also lessen the impact of certain choices and simplify the basic skill leveling.
  
• If you manage to select rest @ exactly 30% energy, you will get a "breakthrough" on the next skill you level. It is best to work on a skill that is a little behind when you have access to this bonus.
  
• Each character path has an associated Sin or Virtue that the player must have at max in order to win the heart of their true love! This is achieved by making dialogue choices associated with each sin / virtue. *Note: to unlock some romance endings; opposite or contradictory dialogue choices must be selected. You can view your progress on each by clicking the wooden-looking button marked status in the top right hand corner of the screen. From there, click the tab marked Virtues.

virtue / sin stats page

• While It does turn the game into a bit of a 'clickfest' I'd recommend getting each skill to its' next required level before proceeeding with leveling another basic skill. (When you are at sea, you have nothing else to do anyway) Typically professions need skill levels in a ratio of [(a+1):a]
  -> a dominant skill vs a secondary one

Ex -> Dancer profession / Lora romance requires the player to level endurance (navigation) and charm (kitchen girl).


basic skills page

These stats must be at level 10+ and you must have a romance level of 100 with your chosen character to unlock the desired ending! Unlike with profession endings, where the player must select the ending in their status book, romantic endings will typically unlock on their own through a semi-randomly occuring event after the player has met the needed requirements.

• Occassionally after completing your daily task, you may be invited to go out to the pub. Always go! Speak with your desired romantic interest for a +1 - +2 romance boost.

the pub


friend selection screen

When Heileen has reached level 10+ in an advanced skill and aquired the maximum value of the associated Virtue / Sin; the player will then have the option to unlock a profession. Open the status menu. Click on the tab Professions. Select the desired profession and click it. THIS WILL END YOUR GAME AND UNLOCK AN ENDING


professions page

• To obtain level 10 in an advanced skill you must first obtain around level 12 in two subsidiary basic skills that are specific to each profession (*Iist appears in above figure)

Wisdom: Read Books
Cunning: Accountant
Strength: Swab the Deck
Dexterity: Lookout
Endurance: Navigation
Charisma: Kitchen Girl
Discipline: Keep a Logbook

• After you have located all of your friends, aquired an advanced skill, and are now able to leave the ship while in port... DO SO. This is how you level the advanced skill directly. Your proficiency in the basic skills has a positive effect on the speed at which the advanced skill levels.
  
• Make sure to select most dialogue choices associated the chosen path!

• Bring a profession-related friend! While you lose energy at a slightly faster rate than you would doing the job solo, bringing a friend adds a +3 - +5 bonus points to the advanced skill. WORTH IT.

Teacher: Kindness + teaching: Discipline + Charisma; Take Marie
Abbess: Chastity + Faith/Praying: Wisdom + Discipline; Take Black
Captain: Pride + Leadership/Public Speech: Charisma+ Discipline; Take Morgan
- Max kindness, pride, chasity

Woodcutter: Diligence + Woodcutting: Strength + Endurance; Take Jack
Farming: Patience + Farming: Endurance + Strength; Take Robert
Cook: Gluttony + Cooking: Endurance + Dexterity; Take Marco
- Max patience, diligence, gluttony

Herbalist: Temperance + Herbalism: Dexterity + Wisdom; Take Ebele
Cabin Girl: Humility+ Repairing/Carpenter: Strength + Dexterity; Take John
Pirate: Envy+Fencing : Dexterity + Strength; Take Juliet
- Max humility, temperance, envy

Missionary: Charity + Medicine/Missionary: Discipline + Cunning; Take Elias
Noble: Sloth+Decorum/Diplomacy: Wisdom + Cunning; Take Sebastian
General: Wrath + Logic/Chess: Cunning+ Wisdom; Take Jonathan
- Max sloth, wrath, charity

Dancer: Lust + Dancing : Charisma+ Endurance; Take Lora
Merchant: Greed+Trading/Merchant : Cunning + Charisma; Take Otto
- Max lust, greed

from Winter Wolves

John
Profession Choice: Carpenter
Sin/Virtue: Lust (high stat) / Dilligence

- When John asks you to help with the sails "Agree to help.": +5
- John offers Heileen some wine "Accept the offer.":
- When John helps cleaning "Don't fasten it.": +5
- When John is waiter and invites you in the kitchen "Eat it in the kitchen.": +5
- When John knocks at the door and is raining "Let him in.": +5
- When he's sad about how he is dressed "Tell him you don't care about the way he looks.": +5
- When he's scared to go with Elias "Give the money.": +5
- When Heileen distributes money on the bridge "Give him more money. He's going to need it, with all those women.": +5

Jonathan
Profession Choice: Playing Chess
Sin/Virtue: Envy / Chasity (high stat)

- When you pose for him as model pick "Scold her.": +5
- After watching him play chess with Otto pick "Offer to pay for his stay.": +5
- After you lose playing chess with him in your cabin "Compliment him.": +5
- When you're in the kitchen pick "Ask Jonathan to help you.": +5
- When you find the love letter "Don't read it.": +5
- When talking about art as way to get immortal pick "Agree with him.": +5
- When Heileen tries to paint "Calm down and finish the picture.": +5
- When you talk about books "Orlando Furioso by Ludovico Ariosto. I've always been inspired by the morality it promotes.": +10
- When you discover he sold your portrait "You could have asked me for the money!": +5

Morgan He is the most handsome.
Profession Choice: Public Speech
Sin/Virtue: Wrath / Kindness (high stat)

- When talks with Heileen of her friends, if you pick "John" +5
- When they talk about Adam, pick "It is.": +5
- When you watch the stars with Marie, pick "Do nothing.": +5
- When you bring food to Morgan/Juliet and you stumble on the ground pick "Laugh with them.": +2 In the same scene, pick "Eat only a few of the biscuits.": +5
- When Morgan and Sebastian fight at the tavern pick "Get angry at Sebastian.": +5
- When Morgan gives extra money to Heileen in the pirate cove pick "Tell Juliet you're just going to give away the money.": +5
- During the misunderstanding of the engagement ring scene, pick "Wish them luck.": +2
- When the poor child ask money pick "Give him ten gold coins.": +10 and later in the same scene "There's no need.": +5
- When Heileen declares her love to him pick "...have something other women don't. I'm pure.": +10

Sebastian

Profession Choice: Diplomacy (high stat)
Sin/Virtue: Gluttony (or Wrath) / Patience

- When you follow him and find he is stealing from Morgan "Push him away.": +5
- When he challenges Morgan at throwing knives "Volunteer.": +5
- When he tries to force you to go in the tavern "Threaten him.": +5
- When you are at the tavern with the others "Drink to your heart's content.": +10
- When he asks you to cuddle with him "Accept the offer.": +5 later in the same scene pick "Don't give him anything.": +5
- When you're caught while spying "Play along and be convincing.": +5
- When you follow him and think he's dead "Cry.": +5
- When talking what you'd do with a lot of money "Buy extravagant things for myself.": +5


Ebele
Profession Choice: Herbalist
Sin/Virtue: Pride/ Temperance (high stat)

- when you invite her to climb the mast "But I want to share the view with you!" +5
- when the guide asks for money "Offer some coins" +5
- when John suspects her cheating on Robert "Wait to hear an explanation" +5
- when talking about kola nuts "Inquire more about the culture" +5
- when Robert gets jealous "Tell Robert to calm down" +5
- when she asks your opinion on her writing "Admit that Ebele has room for improvement" +5
- when Lora offers you food and drink while writing Ebele's book "Have a bit, but keep concentrating" +5
- when Juliet ask Ebele for money "Cover for Ebele" +5
- when you are writing the book's introduction "Persist" +5

Juliet
Profession Choice: Fencing
Sin/Virtue: Envy (high stat) / Kindness

- when Morgan asks Heileen to help Juliet clean "Insist on helping her" +5
- when you spar with her "Compliment her skills" +5
- when she criticize your accounting work "Be a perfectionist" +5
- when she invites to come closer "Stay put" +5
- when she tells Heileen she shouldn't do heavy tasks "Thank Juliet and go back to work" +5
- when she teaches Heileen how to use the nocturlabe "Try one more time" +5
- when she is sick in bed "Offer to apply the ointment" +5
- when she is injured "Insist on helping" +5
- when she confesses "Calm down and inquire about her relationship with Morgan" +5

Marie
Profession Choice: Teacher
Sin/Virtue: Wrath / Dilligence (high stat)

- when you go working in the field with her "Continue working" +5
- when she wants to go in your place "Let her go with Morgan" +5
- when Marie judges Sebastian "...I totally agree with you" +5
- when you visit Jonathan in his workshop at night "Talk about books that she might know" +5
- when she plays a game of dice with Sebastian "Slap Sebastian" +5
- when Heileen finds the cake "Wait for Marie to thank her" +5
- when Heileen stumbles and the herbs fall down "Pick them up" +5
- when Elias visits Marie "Give Elias some money" +5
- when she thinks you poisoned the cake "Humor her" +5

Lora
Profession Choice: Dancer
Sin/Virtue: Lust (high stat) / humility

- when Lora admires Juliet body "Tell her she looks better." +5
- in the beauty contest: "It will be a tough battle." +5
- when she is drunk with Jonathan "Throw them into the ocean" +5
- when you caught her kissing Sebastian: "Tell him he's wrong" +10
- when Lora offers you a massage "Hesitate" +10
- when she wants to buy you a present: "Let her buy something for you" +5
- when Marco makes cookies "Start eating" +5
- when Heileen is sick and Elias visit her "Give him some money as a donation" +5