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Item drops from enemies or from a crate but the item drop is random and the possibility that an item drops is random. To increase the chances of itemt dropping play with another person as opposed to solo.
For this achievement you need to buy the Baby Carrier. The developers suggest playing 1-1 Happy Nut Road : Farm Town to get the item drops.
If you're a level higher than 10 while playing 1-1 you'll find you'll never get loot drops. To fix this problem play either with a second controller signed in as a guest or a friend who is lower than a Level 10 through a custom match. Either way the second controller or friend should choose 1-1 and should start it instead of your main account.
If you're playing with a second controller but have trouble controlling both controllers run ahead of the level to get the second controller killed. Once the second controller is killed you do not have to worry about camera issues or not being able to progress because the second controller is behind the level.
While playing the level make sure to shoot the loot crates.
Personally using the second controller method I was able to get the item even though my character was around Level 45.
If you do not have enough nuts to purchase the items then replay a Normal or Hard roadblock level solo. Personally I replayed the first Downtown Roadblock in Normal.