So i'm barely scraping by with about $10 each day, so I heal my family members, but then at the end of Day 8 I got 'Your Uncle has died'...so I healed my Wife and Son, to which when I hit the 'sleep' option, I got a screen saying the whole family was dead!!

What the hell did I do wrong?

The ghost of your dead uncle murdered your surviving family. Obviously.

So i just needed the Ghostly Uncle Prevention upgrade? Thanks man! :D

Seriously though, if you fuck up the first couple of levels where its easier to get some cash together for whats to come, are you ultimately always boned? I All my family are always 'Very Sick', even the Day after they get medicine! Maybe this is because i never had enough to pay for heat or food in the first few days?

I just make enough to get medicine, but then they die the day after anyway!

The bottom line is that you need to improve at quickly and efficiently clearing people at the border. Those first few days when you barely have anything to check should be easy money. If you're only bringing in $10 (isn't that only clearing two people?) on those early days, you really have no chance later on.

Have you tried easy mode? I have no clue what it does, but it might be worth giving it a shot if you're really struggling.