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Colonel Bogey

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I tend to go for a demolitionist first and then like doctors.

I usually build slowly with everything close together within a neighbourhood (which will probably play well with the supply lines update) and if I venture into different areas I'll attack thug buildings and raze them thus giving rival factions less ability to build rather than expanding into those places*.

How are you playing it?

*Obviously you're forced into expanding everywhere for the win condition but you can weaken opponents in the early game this way.
 
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Feeona

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I'm a coward because as much as I'm all about "PUNCH EVERYTHING, NO HEALS", I absolutely hire a doctor at the beginning of the game.

Most of my beginning plans are running around buying rackets or raiding them to make money to buy more.
 
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Andre Bolkonsky

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I have a very tried and true strategy.

First six months, Boss solos. He opens the entire map, kills every thug, loots every crate, including those hiding in the railyards and dockyards. As the only shooter, his rep goes up dramatically and the amount of cash available from hits and sale of unneeded weaponry put me in a very good position going forward. A fair amount of healing kits fall to keep you in tip top shape so the doc is not yet needed - assuming body armor falls fairly early.

Then you go shopping for henchmen and make war upon your enemies. You aim your rep at the henchmen you want and attain it before you go shopping. You make Goldie Garneau your friend and keep her close, you kill Maggie Dwyer if she shows her body art anywhere near you.

Repeat as needed. But Angleo Genna, his knives and the Golden Service Revolver are sufficient to take out most anything, even a small building.