Charityware
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The OLPC Foundation could set up a software development site and software store for charityware (a combination of sf.net and shareit.com, e.g. using SourceForge Enterprise Edition [1]) with the revenue going to the OLPC Foundation. A group of employed developers could help to improve open source software or locally developed software to make it sufficiently interesting to be accepted as commercial software. The enhancements could optionally be released into the open source after 5 to 10 years.
As a side-effect this could attract software developers into an OLPC community that would also develop for the OLPC laptop.
Firefox browser
An enhanced Firefox browser could, for instance, allow extension through webstarted Java add-ons and plugins. (Enhancement of Firefox could be outsourced to a Java vendor (e.g. Sun or IBM), who would in turn get a revenue share from selling a license for his VM.) The Mozilla Foundation hasn't yet shown any interest to go that way so this could be an interesting market niche. Java add-ons and plugins could then be sold in the shop, too. Webstarted add-ons could stay conveniently available once bought for an account, even after being discarded locally. Selling the browser for $0 during the first month could help to establish a user base; alternatively one could hand out a limited number of invites to contributors. (Employing the same psychological effect as artificial scarcity in laptop software: If something is scarce it may seem more valuable).
An interesting add-on could, for instance, be a travel management solution with reservation services provided through certified OLPC travel partners, LDAP access for users and travel policies and automatic feedback to Mozilla Sunbird calendars.
One could also embed a nested-X server (or WiredX?) into the browser and run an OLPC emulator in a Unix jail environment from a browser add-on, with other web clients in the same virtual mesh network. The browser could then webstart OLPC activities from URLs, which is convenient for the casual user.