A lot of great ideas in this thread!! I've automated quite a few work tasks over the years(just as fun IMO) but the ones I've done for 'fun fun' are...

- I played an online survival game and the server I played on had a live web based map that you could look at, the server chat activity was also visible on this online map and no one playing on the server could tell if anyone was listening in, the problem was that the text disappeared every few seconds - so I made a script to check if the site changed at all(passively listening for the js event, scrape the text, upload it to my private server via FTP and I setup a webpage that any of my friends could logon to to get the full details(with various sorting/filtering options as needed, nothing over the top, and updated every 30 seconds) this helped me and my clan tremendously because it gave us a deep insight into all the alliances, who raided who at which times, then we'd use this edge to make new allies and we eventually completely crushed the top clan of 18+ people with our smaller group of three.

- Ran a gaming server for a year or so and I automated checking who had previous bans on steam for any game(it was some online service, don't remember which), got their SteamIDs off of server logs, performed the check, and if certain values showed up on the page it would log the query page to a screenshot(to get a full picture of their activity in case of dispute), log their SteamIDs in a list and the ones who got red flagged got banned nightly.

- 2 MMORPGs(one top down game, and one 3D game), got to max level on the 2D game without playing a minute of a new character after script was done(python, image recognition, basic evaluation of status/reaction) and returning to a character with plenty of loot when getting home after a day at work was a lot of fun. (some of my purist gaming friends don't agree, but we all get our kicks differently) - I never traded to not affect the economy, was done as a learning challenge, and the results didn't matter a whole lot. Quit playing pretty much right after 'beating' the challenge.

- Polls, multiple personalities, statistical variance.. the whole 9 yards..

- Photoshop workflows, and a few other 'art' related programs. I can only do something manually for so long before I'm itching to script it.

- Web scrapers of all kinds, several image scrapers, one which filled a folder with results from a keyword of your choosing.. another one is classifieds scraper which notifies you when something you're looking for appears, done by indexing current status of the sub category you're interested in, run a diff, pop the older ones, stores all time stamps/ID's/URLs, browses to the new ads and gets relevant fields, formats them all in an XLS sheet for friendlier and ad free browsing(with links to images).

- Text manipulation for a big keyword project that spanned months, ended up with lots of great data, some of which is no longer available accuracy wise.

- Scripts to check the status of and update common applications silently and over the home network. Other scripts to check the status of all devices on the network, the 'health' of various services etc..

- Backups.. file manipulations..(data, names, inserting metadata, reading metadata from thousands files, indexing the results and subsequently performing actions to the files based on the metadata)

- Some hardware quirks that I ended up fixing with scripts which automated devcon.exe actions and that ran on boot.

- Online dating, top three spots constantly, and yes, more eyeballs on your profile means more first contact from the ladies. The profile was meticulously written and re-written based on performance(contact stats), with ad copy type hooks intertwined, my record day was 17 new messages.