In the days before computers and big filing cabinets and other ways to enhance organizing and listing things, taxes generally were on simple, easy to coral revenue sources.
Tarifs were a great one; any ocean-going port would have a tax officer. I suppose you could off-load in some podunk fishing village, but try moving a ship-load of goods one horse-cart at a time. By the second convoy of 30 or 50 carts, assuming you could find that many, someone would notice. There was a government representative and some sort of authority garrisoned nearby, and the business people you dealt with knew they could lose a lot of money in fines for buying your imported beer or tea.
Look at the Stamp Act, which went along with the tea tax - an official stamp on legal documents, for example. You want it made official, you pay the government. Your taxpayer comes to you. If they have eough possessions to worry about legality - of a contract, land sale, etc. - then they have incentive to pay up.
Same thing - you didn’t worry about retailers, you went after the manufacturer or wholesaler - liquor taxes, for example. How big a distillery can you set up before someone notices you’re there and decides to demand payment? Even if you hide it in the woods, soone or later you’ll be tracked down. You can only haul so many cartloads out of the woods before they start following the tracks backward.
Millers (the kings in the good old days loved to tax grain); the convenience of having your grain done in a short time in a big mill beat the effort of using a small grindstone at home.
the wild west was fine for people spread out and barely established. Once you switch from ranches miles across to farms in quarter sections, the government infrastructure is there to ensure you pay a land tax, land transfer tax, even a poll tax if you want to vote, etc.
Still, the best way was to tax the big businesses that couldn’t run away or hide; tax railroad revenue, manufacturing, and imports.
The best system way back when was the Roman Empire’s “tax farming”. the emperor granted taxing rights to the governors, and so on down the line. The governor could do what he wanted as long as the em[peror got his required amount, so any lifestyle enhancements came from upping the rates even higher. At the bottom, there was the actual collector - IIRC St. Matthew was one. They were empowered to collect a certain tax from a certain area, in return for a share - hence the incentive to be persistent and nosy. Oddly enough, the people who were squeezed by unreasonable levies did not like the collectors.
Keep in mind that in the days before automobiles and phones and giant cities of impersonal anonymous apartment buildings, the world was a lot smaller and everyone knew each other’s business. As anyone from a small town will tell you, everyone is nosy and gossips; so you could not keep a secret like having lots of money or a secret business. In fact, a lot of crime in those days was along the lines of “they broke into the old man’s house and killed him looking for money, because the gossip was he had a fortune hidden in his poor little house.” Gossip does not have to be correct - it just has to excite the authorities to investigate.