Cute game, but the buddies seem weak compared to click upgrades and finding cash in the trash cans is the most impactful because it scales so fast (I hit the goal amount by accident purely by finding cash). I tried to get all buddies on my second play, but my money went so high from cash drops that it overflowed into the negatives and I couldn't buy anything anymore.
I also don't know if it's intended that the same buddy can drop more than once; I got the first three in order on my first play, but replaying got me the possum and raccoon first, then the bat, and then the possum and raccoon again.