Say hello to the Troidovski family:
Our fearless wagon leader:
Destre Troidovski
A blacksmith from Missouri, Destre is a formidable man who has literally torn a bull in half with his bare hands. An entire. Fucking. Bull. Eventually he settled down with his wife to figuratively tear her in half instead. When he isn't bench-pressing exactly 792.34 anvils, he spends his free time writing a novel on his pectorals and growing an epic beard.
His wife:
Mary Jane Troidovski
A sly and controlling woman, Mary Jane more often than not is the one holding the family together. She resents Destre's business in the smithy as he always tracks ash onto her nice clean floor, but she tolerates it because she knows her limitations as a woman in this day and age. While she usually means well, she can sometimes be a real biatch.
Their son:
Digit Troidovski
Digit is the first son of Destre and Mary Jane, and their inexperience shows. He has four thumbs, hence the name. He also has a bizarre obsession with sharks that have Winchesters attached to their heads.
Their twin son and daughter:
Herpios and Herpias Troidovski

A pair of twins born recently. Herpios is a male and is horrifically deformed, while Herpias is a female and is oddly normal compared to the rest of the family. The two are extremely close, but they are able to handle being separated. Herpios loves corn.
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Dessie hunny, did you remember to do your shopping today? Remember dear, we're leaving tommorow!

Uh, yes. Yes I have. I took care of that weeks ago, dear.

Good, cause if we don't leave tomorrow I am going to cut off your goddamn dick.

Wait what?

Nothing Dessie, just get the wagon ready. I'm going to go out with some friends, so be good okay?

Yes'm.

DIGIT! GET OVER HERE YOU LITTLE SHIT

*sigh* Yeah?

Take this cash and go by Matt's place for me while I pump some steel.

No.

DO IT FAGGO...I mean, uh...I'll let you buy some candy. And stuff. Yeah.

Dad, I'm
seventeen, I'm like, sooooo over candy.

Let me put it this way. Either you will go shopping for daddy, or daddy's belt will come off. And we all know what happens when daddy's belt comes off.

FINE, I'll do your stupid shopping. Geez.

Oh gawd what did he say to get?

Ah, thanks for the advice Mr. Matt.
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Reader Input Time:
What should Digit buy for the long trip to Oregon?
Buy like 40 fucking oxen. Haul ass across the country and reach the end before you get hungry/cold/dysentery.
1 hat
12 grandfather clocks
nothing else
Metagame. Buy some bullets, kill the shop keeper, take everything? Or just get some toast.
You have died of dysentery.
All you need is a hat and 12 grandfather clocks...
GODDAMNIT LUCASHOAL!!!
I wish I could actually do a playthrough with 12 'clocks and a hat...I'll probably do an LP for Oregon Trail II if I have time after this one, just to do that.