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I am not a lawyer, but consumer protections should generally kick in when an issue is actually evaluated in a court. If you are being charged for things you believe to be unfair, you would need to refuse to pay, then see them in action after the business escalates it. Often, a predatory business will give up when it knows it doesn't have a case. But it's pretty hard to work on behalf of a citizen if they ultimately are convinced that they do have an obligation to pay after all.
I agree with the other commenter on the first issue. If you have been paying the amount you were charged, and then hit with surprise retroactive charges, you would have a serious case in small claims. I expect a judge would favor you if it's as described. $1000 for late fees is exorbitant, especially when the glitch was from their software and not rectified quickly. Unless you're leaving out relevant details that explains the situation better.
For the second issue, needlessly cumbersome cancellation processes are considered dark patterns and may be illegal in some cases. These cases are being enforced more recently, even against large companies like Amazon. For your pest control case though, if you face pushback when cancelling it's pretty simple to tell them you won't be using their services and will refuse to pay. If you already paid, you may be able to issue a chargeback after explaining the situation to your bank. Seeing as how you would be being charged for services not done, I don't see how the business could contest that after being informed of the cancellation. You would still be on the hook for a (reasonable) cancellation fee, as lost business from a cancelled reservation does represent real damages.
We are a country with a litigious history and we have recognized considerable rights for consumers. Just because you feel powerless doesn't mean you are.
I'd wager that his lease has a mandatory arbitration clause that requires him to pay up front then try to get it back via arbiters chosen by the landlord.