Well, the landing-fee thing is pretty variable. As a pilot of a small plane so slow that it can be out-paced by a lot of cars driving these days, I tend to stay away from big airports like O’Hare, LAX, and LaGaurdia since flying my little 2-seater in there would be a lot like skate-boarding down an interstate. But if I did land there I would have to fork over some change.
Not everybody gets charged a landing fee. The airport in Lafayette Indiana, for instance, does not charge these fees to student pilots. Some airports only charge landing fees to commercial operations, or only to airplanes over a certain size. Fees are also variable in some places based on the size of your aircraft, weight, number of engines, etc. At Meigs Field in Chicago, for instance, last time I checked it was $27 for me to put wheels on the pavement, but some business twin-engines get charged hundreds of dollars for the same privilege. In some places, the landing fee is waived if you buy gas or something else.
For a general aviation pilot, you get charged after you land. Filing at the time of flight plan wouldn’t be practical - you could divert from your plan, meaning you never land at your original destination so the fee would need to be refunded, or maybe you wind up diverting to a fee-field mid-trip, in which case they’d have to collect after you land. Also, if you’re flying under “visual flight rules” you aren’t required to file any flight plan at all, even if you fly from one side of the country to the other. Flight plans in this country are only required for instrument-based flying or crossing the US borders. On a nice clear summer day most general aviation flights drop in to airports without prior notification. Anyhow, there’s a front desk where you hand over money for fuel, oil, and anything else you need to pay for, including landing fees. There are always folks hanging around at these places watching what’s going on. If you land then take off without paying they write down your tail number (unique to each airplane) then go to FAA to find out who owns the airplane and come after you with a bill. This also brings you to the notice of the FAA, who can make your life very unpleasent if they choose to do so. It’s debatable which is worse - an IRS audit or an FAA investigation. If only for that reason, most folks pay up honestly.
There is a rural airstrip out here (and we’re using the term “airport” very loosely in this case) that has the audacity to charge a landing fee. It’s basically a divot carved into a cornfield, at one time paved but not maintained since (I think they have a fish farm in one of the potholes), and the centerline must have been painted by someone under the influence of something because it wavers back and forth, most of the time being a 1/3-2/3 line rather than down the center. The owner generally plays the role of “airport thug”, if he happens to be around at the time. So you get the occassional spectacle of a John Deere chasing an airplane across a field with the tractor driver screaming dire imprecations at the pilot. I don’t know if he ever collects or not. Last time I flew in there he wasn’t around, and I was almost disappointed. There aren’t a whole lot of things you can outrun in a Cessna 150, but a farm tractor is one of them and it would have been nice to NOT be the slowest thing around for a change.