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In the most extreme example, let's say we're talking about some misguided site who got the wrong idea that PR hoarding was a good idea and had no outbound links visible to the SE's. Though there are always exceptions, no outlinks generally might suggest a site that was being manipulative. Again, there are exceptions, like product pages or something, but if an entire site has no outbounds? Hehe. Prolly hurts that site.
Conversely, add relavant outlinks to a site that had been PR hoarding, and that site prolly benefits, quite possibly even very short term. But that is an extreme example.
Remember that it has long been the case that sites are evaluated by their linking structures. "Hubs" in older search papers (e.g., directories) were/are identified primarily by their large numbers of outbound links. IF those outbound links are well organized, topical and consistent on any given page - and link to other quality resources - then the linking site might well be viewed by the SE's as a valuable. More so if the linking site also has lots of inbound links, essentially confirming its usefulness by virtue of others' votes.
Point being, sites are generally rewarded for being good Netizens and that involves, in part, linking to ther useful and related resources. Just like sites are less well rewarded if their outlinks are non-existent, or off topic, or point to bad neighborhoods, etc. It's hard to quantify, but definitely real.
I'd also note several years ago, when this became understood by many those looking at the algo's, all the sudden, thin affiliate sites started adding topical outlinks like crazy, and I'd say to some good effect. Like all aspects of the algo's however, that rather overt approach may not be very effective anymore.
Essentially, today, the more natural the linking pattern as perceived by the search engines, the better. And it's natural for most sites to link out on at least some of their pages. Keep in mind too that the SE's are able to associate and cluster certain kinds of sites and evaluate them in that light. So for example, directories have certain profiles, as do news sites, e-commerce sites, etc. And they are likely evaluated versus their peer sites.
This is perhaps one good way to look at it: Three different sites (and three comparable internal pages at each of the three sites) being otherwise equal, if site A's internal page linked out to a relavant page at CNN or wikipedia, and site B's internal page linked to a decent external site but less authoritative than CNN, and site C linked to no sites at all, which of those three pages would you intuitively imagine the SE's would most favor? ;-)
Linking out - helps your rankings?
Linking out to relevant on topic sites makes your site more valuable to your readers/visitors.
Since some of your readers/visitors readers are likely to be webmasters of relevant sites they may well link to your site partly because of the added value provided by the links out from your site.
Get enough new inbound links like that and your ranking in the serps may improve.
On a pretty well-received site in google and yahoo, I've recently added a few relevant outbound links to each article in an article library(almost 150 articles). We're in the personal finance sector, so there are plenty of .gov and .org sites to link to.
My goal was to increase our authority in the eyes of google, and it's seemed to work. Over the past two months, I've seen increases of 20-30 spots for some of our most competitive keywords. It's hard to draw a direct correlation when an entire campaign is being made, but I can say it certainly hasn't hurt us due to any 'link popularity leaks.'
In the end, I think it makes our article library much more user-friendly and gives good places for further reading and more in-depth research. That's the goal right -- make good content and google will find you? Well... let's not get too ambitious :)
At any rate, it's hard to argue against adding quality outbound links in appropriate sections. Who knows, if a real person thinks it's quality material... it might just get you more inbounds... legitimately.
Just my .02
Try to only link to sites that are the top ones in your industry
If I'm giving away links, I like to find "undiscovered gems" that are highly relevant, rather than adding link support to sites that are already strong. The big guys will hardly notice your link, but it's very satisfying to make a positive difference to someone who is just starting out.