As a non-cable subscriber I typically have a difficult time watching live sports unless they appear on ESPN3.com (thank you Xbox!). As such, I've grown accustom to the shadier areas of the web looking for free streams. To be honest, I just don't care enough about television to pay so much for it every month, especially since only a handful of MLS games will be shown on FSC this year.
Anyway, my point is that, given MLS's youth and willingness to utilize technology, we have access to one of the best live streaming packages of league sports in the nation.
Match Day Live is MLS's pay-per-season streaming service. While it's not without its own faults (it uses Silverlight, blech!) it's certainly the best way to keep up on everything that's happening around the league, especially for those non-nationally televised matches. This is especially helpful for those of you who are fantasy league players (of which I'm one as well).
So here's the deal. The season pass costs $40 right now ($60 after 3/28) and gives you live, HD streams of all games not being nationally broadcast by either ESPN or Fox Soccer Channel (I'm not sure about Telemundo games). In addition, throughout the season you are able to re-watch archived matches, again in HD. Some play-off matches are included as well.
So, when all is said and done, you'll have access to roughly 150 matches that normally wouldn't be aired in Portland.
Now, for we Portland Timbers fans, there's a caveat here that kind of sucks. If you live in the metro Portland area chances are MLS will have you blacked out due to a deal with our local TV broadcaster. This is common practice amongst every team/metro area. As such, we won't normally be able to watch away Portland Timbers matches via this service.
Now, I can't say anything directly (given this SB Nation policies). But I'll just leave this LINK right here. That LINK will be very helpful in helping you enjoy the Portland Timbers. That's all I can say.
Despite blackouts, I've found over the last couple years that Match Day Live is a really solid service for not a lot of money. If you have a decent internet connection I see no reason why this service can't be an equally great for you.