I still think Futurama holds up well. I still find it as funny now as I did then.
Regarding the show's "tech": I agree that much of the show's depiction of the future doesn't make a lot of sense. Yes, it seems odd that in the year 3000 people would be still using dial-up internet and VHS tapes when they're old hat now, and pretty much everything about the robots is absurd. I mean, take the Robot Mafia; who would build robots to be criminals? What purpose do they serve? Same deal with Tinny Tim; who would build a robot to be a poor orphan? Or how about Flexo and Angleyne being divorced in "Bendless Love"; why would robots need to get married in the first place, let alone divorced? Or Santa-Bot? If the people of Earth know what planet he lives on, why haven't they sent Earth's armies over to Neptune to destroy him? After all, he's just one robot.
The Old World robot village in "The Honking" kind of make sense, if you apply the thinking of the Red Dwarf episode "Meltdown" and assume that the village was originally a theme park attraction and in time the robot inhabitants learned to break their programming and have become capable of independent thought, well, almost: as one robot villager put it: I choose to believe what I was programmed to believe!"
No, a lot of the technology on Futurama doesn't make sense; but I'm usually willing to chalk that up to simple "it's a cartoon, it doesn't have to make perfect sense" logic. If you want a canonical reason for the anachronisms, one could recall "Space Pilot 3000", where over time, civilization was destroyed and rebuilt not once but twice, so perhaps mankind lost some of its' past technologies and by the year 3000 had to start over again from scratch.