To Google, a link to a site is vote for that site.

PageRank "leak" is a misnomer because you will not lose any PR due to the link, unless the link leads to a site in a "bad neighborhood" or is bouncing back to the same site (internal link). If the outbound links are simply reciprocal links, then neither site will gain any advantage.

If the sites you link to are related in some way (related business or subject) to your site, then these links could simply be considered part of your site's content, so no problems. Now, if there is a list of 50 links on the page, Google could very easily consider it a link farm and penalize the page, if not the site.

If you are not sure, just ask yourself if the link is adding quality content to your site, or simply to manipulate your PR or SERPs.

In the end, content wins.