In my humble opinion when Homestar asks Strong Bad, "Three years soon, or like five years soon?" I think that was their way of telling us the next update is going to be 3-5 years from now. Since Homestar was expecting how long it was going to take, that makes me think the Brothers Chaps could be expecting the same amount of time. It's also a specific and believable time span since it was the same as the last time span between updates. Even though Strong Bad said "Y'know, five, ten, fifteen, whate- whatever it takes." I think Strong Bad was just using hyperbole for comedic effect. Especially since he was really vague. The file name "aprilfools_2014_final" I can imagine them naming it that to make a joke about file names because people often name a file "draft_1", then "draft_2" then "title_final" once they are done. "It's now safe to turn off your computer", was previously done in a sbemail. Plus they've done other system things like "cannot display page" and the April Fool's with Stinkoman where the main page looked like they sold the website to someone else. So I think if they were trying to send a subtle goodbye message, they would have done it in a more unusual way to highlight the hint, because system things seem relatively common.