Protip: go around the upgrade map, and look for things in this order:
1. Power Generator
2. Coin Bonus
The rest of the stuff will come naturally as you go for these. The TVs are worth a double upgrade that you can choose.
i don't understand why, in the later on africa endings (2035), when you put the earpiece in, you arrive in cancun. so Future Todd killed angela and her husband, then somehow got rich? or he decided against it, went with some other girl, then got rich somehow? the latter doesn't make so much sense because there is no in-universe reason for him to decide against it here and not other endings.
Anyway, to get the badge, start out buying the ice cream hat. Then go to the menu (has to be DURING a workday) and put it on. Next, buy 42 papa posters (the $5 one) and 8 small flags ($25 each). Then work on buying the machine upgrades. When you get the ice cream hat achievement, switch to the next hat. Try and get at least 20 "goods" at each station, and by day 16, you should have the badge. You can get it sooner if you get a lot of "perfects" all the time, but that's not worth the effort.
i hate whoever put this in their list for the yo dog quest. mine involved actual good games like amorphous+. which by the way, was one of the first to popularize achievements, and would fit into an anniversary quest perfectly. sigh.