Mos Eisely is a spaceport. Anchorhead was doughnut center, (what a hole) and presumably was more of a little agrarian community linked to the moisture farms. There are probably a lot of Anchorhead type towns on the planet. Probably a lot of "ghost" towns too.

In the OT, M.E. is presumably the major destination whether arriving or leaving Tatooine, unless you're doing something really really shady, and are willing to risk landing somewhere like the Jundland Wastes. And even a tiny spot on the map in our world can have a large international airport.

To borrow a term from Star Trek, there's a "failed colony" aspect to Tatooine. A lot of settlers probably tried to make the miserable rock green, and only the descendants of hardier souls are still there trying to make it work.

I got the impression from the OT (and the deleted scenes with Luke's friends that were in the comic) that the Empire normally wouldn't bother with such a remote inhospitable place. They have bigger fish to fry, so maybe there's a spy or two just to keep an eye out for Rebel activity. Which is why smugglers and the underworld would have a presence there.

The Empire probably doesn't care what Jabba and his ilk do so long as it doesn't interfere with their plans, and perhaps an Imperial official gets a annual bribe to keep looking the other way.