Software updates are costly, resulting in increasingly complex and untrustworthy software that slows down over time. The author suggests using software with fewer users, easy to modify, open source, and with fewer updates. The simplicity and niche nature of the software makes it easier for forks to keep up with and modify, as opposed to monopolistic, feature-packed software. The author recommends situational software, which has a few users who share a context/situation, to minimize software complexity and avoid the need for upgrades. The focus on small, easy-to-modify software promotes experimentation and small, niche app development that serves specific needs.
http://akkartik.name/freewheeling