Edit: Do those beginning options have that much impact on how the game plays out? I figured the game would play out more or less the same regardless of what you choose at the start.
After few tries what worked best for me was full academic background and from the abilities - sharpshooter, brainy and healing implant. Also charm and manipulate from the sexual abilities, with the priority on manipulate as charm is easier to train with seduction - caress.
This set of traits means starting with a rifle and some ranged skill and also 60 int which maximizes gain from academy courses (but take Daria's course last as it requires slightly more int for the full reward and you will get int from other courses). After doing at least 2 courses you will also have enough int for max gain from skill books. All these things are one time only so it's better to get the best results. Of course you can play the game with a dumb character but it will be harder. There is no easy repeatable way of training int so it's probably the best stat to invest your starting traits in.
However to pay for the courses and books you need some early game income not to mention upgrading your house and equipment, so before you can improve yourself you should focus on combat for money.
So here is a basic walkthrough:
Take Juno for free as your first slave, give her your starting crossbow and then change to a pistol once you find one. She will still miss almost everything but criticals always hit and raise skill. Your starting rifle should be enough for the first quest, maybe hire one cheap merc for a day or two but dismiss him once done to save money. For slave training do only things that result in nothing bad on failed rolls.
Progress through Kymanto quest line until you get 4k and then hire 2 good mercs. By good I mean combat armor and at least a rifle, I think Mr Doyle and Space Marine are the best ones before you have access to Crystal Hills. Don't worry about their salary, they are well worth the investment. With those two you can start killing enemies on the map, getting bounties and doing other quests for serious money, but you still need to prepare better for the docks fight, preferably getting your 2nd slave and combat armor for you and both your slaves.
Don't forget to sell extra weapons and merchandise at the market in your home area. Some ranged skill training in your house would be nice too. With this team you should have no problem getting money and you can focus on 1500 influence for the crystal hills, mostly from the quests and killing bandits but upgraded home is a nice source of influence too. Once you can go there the arena is an easy money source every day. The team you already have is enough for 2 random easy fights without even getting hit once and that's like a quick 400$ every day. Work on academy courses and books for skills and after that the game becomes very easy.