Lol that's Rimworld for you. Every time I send a caravan, I always send 150 wood, 10 medicine, change their food policy to packaged meals, and make sure I have at least two guards with whoever I'm transporting. If I cannot send two support guards, I just send everyone. Your base cannot be attacked if there's nobody there to attack.
Most of my time spent in Rimworld is changing policies and micro-managing with zones and making sure everyone is doing exactly what they're supposed to be doing. For policies (going off memory here), I always set a summer clothing, winter clothing, and a soldier clothing policy. For food I restrict everyone to simple and fine meals and set a caravan option for pemmican or packaged meals. For drugs, I make sure I restrict everyone to take one Penoxycyline every month, the hard drugs to never take (also set those as part of the burning policy for my crematorium), and set recreational drugs (ambrosia/beer/smokeleaf) to recreational so it keeps them happy.