I utterly despise being caught up. See, when I start a new web comic I try to read the entire archive. I will go through the archive as if it were a bag of chips and I have had years of potato ship famine. (I will also occasionally paraphrase turns of phrase badly when I'm talking about web comics.) Eventually though, I will get caught up. And I will always be caught up at the point where the web comic artist is having a hiatus or a "well, I don't have any updates ready yet."
And then I will slowly go bonkers waiting for the dang update.
The only time that this did not happen was when I tried to get into Sluggy Freelance. The reason why I did not have this occur is because of it being Too Damn Long for Me to Try Reading. (Which usually happens for extremely long running paper comics like X-Men or for certain manga series that never end because the mangaka does not know how to end a damn series so it goes on and on for endless reiterations and you want to strangle all the characters and bury them face down at a crossroads with stakes through their hearts.) In the case of a Too Damn Long for Me series, I generally give up and therefor, don't go crazy looking for an update.
This ramble is of course almost entirely about Homestuck, of which I have become greatly enamored, and which has not yet updated. (I should point out that it took six tries and a lot of utterly adorkable fan art before I could take the plunge and get through the vast silliness of John floundering around doing ridiculous things.) I will probably/should probably re read again in hopes of being able to force my way through the freaking Troll l33t sp33k. (Which I despise with a deep and overwhelming passion, by the way.)
What I'm thinking of doing, since I have Homestuck on the brain is possibly write a "walk through" of the comic.(And probably plan for "walk throughs" of a few other web comics I like.)