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So, the players go on strike, and scabs have to be hired. Fair enough. Why did the cheerleader captain have to hire a whole new squad of cheerleaders? Did they go on strike to show solidarity with the players?
I haven't seen the film in years, so I can't recall if it was covered, but that might actually be exactly what happened. Many times, when one specific area of an industry is on strike then other areas might strike as well in order to show solidarity and support. They might also have been legitimately striking for their own better wages or benefits and coordinated with the players for the timing.
I keep racking my brain on why the mafia thugs would have made Nigel miss kicks in this game. In-universe, the Dallas team is supposed to be so much better than the Sentinels, Dallas would probably have been double-digit favorites (which means that whether Washington loses by three, or wins in overtime), Dallas can't cover the spread. Unless it was some sort of over-under bet, which wouldn't have been smart if everybody's betting on Dallas to stomp Washington, or some sort of prop-bet ("Who wants to bet that Nigel chokes on a field goal?"), or maybe they did bet on Dallas to just win, even though it would have been a (bet $200 to win $100) sort of deal.
Probably the mafia guys weren't the ones making the bets, they were the ones taking the bets. I.e., they'd have to pay out more if the Sentinels won than if Dallas won.
So, the ad Todd and Riley found was meant to replace "uncool" parents with "cool" ones. Now that's an asshole-ish thing to do with your parents because they are not "cool", right? Later I remembered that just about every replacement made ended up in An Aesop that leads to Todd or Riley deciding to undo the replacement. Therefore, it is easy to assume that any other kid who wanted cooler parents will most likely learn that they are no replacement for their true parents and do the same. Todd and Riley were orphans, so they got an exception.
Tasumi's armor being a Japanese Halloween costume in season two may seem like a stretch, but it makes perfect sense. We never see her costume doing anything unusual, and it can be repaired by using duct tape.
Okay so Conrad is Riley and Todd's uncle; I can work with that...except for one tiny detail...WHY ON EARTH DIDN'T HE ADOPT THEM HIMSELF INSTEAD OF JUST GIVING THEM REPLACEMENTS AS PARENTS?! You can legally adopt biological relatives and I'm pretty sure that orphans will be sent to close biological relatives by the legal system if they're deemed fit for adoption.
He explained that he knew nothing about parenting and thus being afraid that he's not up to the task. Also we never seen any suggestion of Ms. Fleemco existing so perhaps he preferred to give them full family and help from the shadows. It is not the soundest thing to do, but people not always act reasonable.