I think in the past Fundraising streams have been proven to make a difference.
The i49 Showmatches are still ingrained in my memory because it was a taste of what we could expect for that LAN in terms of the NA vs. EU matchup. I've donated to the JT fundraiser right after I saw them win the Aussie League, and to the TLR one during the fundraising stream. My point is: if you give the viewer/possible donator a chance to see the team in action and get to see some interaction with them (or even directly interacting with them via interviews with viewers' questions) there will be a lot more empathy and a bigger chance for donations.
Now if there were a number of streams dedicated to getting viewers to connect to the teams/players/scene in general throughout the year, it would create an opportunity for viewers to experience the above a number of times before each of the LANs. Steal some ideas from TotH and have pro players also do jumpmaps, surfmaps, Ultiduo, MGE tournaments, Bball matches etc. and ask them questions before, during, and after to let people connect with them. You can even let people bet money on these matches and give the winner a signed item, while taking the money to put in the pool.
Promote the streams on here and on Reddit/tumblr/whatever and tell people that they are donating for the pro scene in general. Try to make sure that players from every team (if possible) are in the stream. Give shit away for donators, set a goal we want to reach as an incentive, and give shoutouts to big donations. I'll never forget that ArieKanarie donated a boatload of money to the TLR fundraiser and Shitwizard donating to TotH because they made such a fuss about it at the time.
There were 2k viewers at the lowest point at i58, with most of the Americans still asleep. 3k in the afternoon. If - over the whole year - those 3000 people would donate $5 there'd already be $15.000. And that's not even wishful thinking. We just need to get the word out.