I read it over a decade ago and given my impressionable mind and lack of other such "ridiculous" stimuli in my immediate environment i found it hilarious at the time. I also found things such as improbability engine ingenious. Vogon poetry, depressed robot, doors programmed to be cheery, building a computer to figure out what the first computer said. All that was non-linear and mind opening to people back in the 80-90's-ages. Reading it today I could understand that it's not as mind bending since such humor is abundant. I loved star wars growing up but don't think it would blow my mind as much if i watched it today for the first time either. Adams made a great contribution at the time and that's why all the nerds still appreciate him for it.
I agree, it has some fantastic situations, imagination, and probably a product of the times. I just think there is too many examples of it strung together in a completely haphazard way. A condensed version, I think would have been much more enjoyable, and less tiring.
To follow up and mix in a few other sentiments noted elsewhere with my own experience, I'll partially agree.
For me, it's a bit like Monty Python's Holy Grail. I saw it alone as a young teenager and I just didn't really get what the fuss was about. But there were a few things that struck me as brilliant, like the glimpse of the guards just about to throw a cocunut attached to a pigeon just to settle once and for all the movie immersion-breaking issue of how that coconut got there (we don't see if it works). On further watchings the Holy Grail seems more brilliant than I expected, and I've gotten more out of it, but it's... well, hype is hype.
The HGttG style is also a bit unique, often inverting and twisting ideas in a way uncommonly stated. Needlessly so, often. And it just absolutely revels in it.
A word of caution about the series: it starts off with a silly apocalypse and really eventually gets dark. Like you, I may also be placed in the Total Perspective Vortex for this, but I really recommend slogging it through to the sixth book. It's only half Adams or so, but it's certainly a necessary palate clenser after the fifth book and I think it revives the spirit of the first. (By the way, I am absolutely certain both the Question and Answer show up in context with each other, but you've really got to get to the end of Mostly Harmless, and that story is anything but.)
Keep in mind too that nothing about the Hitchhiker's Guide is canonical. It always changes when adapted to TV or radio or movie, and it has a damn hard time being consistent with itself. Which is also part of the fun.