This style of thinking is nothing short of delusional. The open source community has too much of this and too little pragmatism. The split between free software and open source happened because of this reason and we have been paying for it, ever since. Much like the creative commons community, FOSS could have settled on multiple styles of licenses.
Not anticipating tivo, cloud
Unix is a timesharing system used in routers everywhere. Not anticipating patents, tivo and cloud from the day one is nothing short of embarrassing.
Open Hardware
FOSS can not exist in isolation. Firefox and Ubuntu both failed in mobile. Corporations have successfully screwed over FOSS by locking them up in hardware; which is clearly anti competitive and monopolistic. Instead of having general hardware and consumer choice for software we have the opposite. The open source world has never really addressed this issue nor did it forge broader alliance with the open hardware and other open movements.
Open Source as a certification
Instead of having legal requirements for a business entity to call itself “open source” any corporation can pretend to be open source now, when they are in-fact mixed source. This is a drastic failure. Not only could such a legal requirement be profitable for the certifying authority, it would also increase consumer visibility and trust. Now many consumers think they are buying open source when they are just using mixed source products.
PR disasters
Allowing the press to win the GNU / Linux naming battle which was a smear campaign in disguise. Also the usage of the word hacker in media. Being identified with communism and not with indie movement seen in music and elsewhere. The FSF has taken a half assed approach to this instead of using all legal measures to fight the press. No one really knows where FOSS stands. Every sane minded person should be vary of communism and M$ easily played on this fear in the 90s. On a side note, software is not a scarce commodity.
Appropriating funds and time for vanity projects and trifles like Firefox vs IceWeasel
The FSF has diverted more than enough funds on vanity projects like GNU Hurd. Early in the 1990s, Scheme was chosen as the language for scripting FSF projects on the insistence of Richard Stallman. Even now a number of major projects like GIMP are forced to use scheme. You can’t have compulsion and free in the same sentence. It is deeply hypocritical for FSF to dictate language choice just as it is immoral for a business entity to dictate how you should use your phone. The reasoning is here is nothing short of tyrannical. PHP has done more for free software than Lisp. The goal of FSF should be broader, safer choice in consumer software as opposed to any constraints and pointless forks. Customer support, user happiness, developer happiness, safety, transparency and ease of use are more important than crazy architectures and mere openness.
Why scheme ? Why not vala ?
Not building a business model around complements
This is also applicable for the *BSDs. Could FSF have funded itself by offering hosting solutions like digital ocean, selling books and hardware like Amazon, source management like gitlab and so on ? Instead of the D.I.Y attitude FOSS community relies on begging. Instead on yapping on and on about “free” and “open” software money could have the done all the talking. This is how profitable independent labels operate in the music world. Linux could have had an AppStore long ago with payment integrations, issue tracking and what not! Most open source projects don’t even collect email addresses of people who download and use their software. Only paid users getting priority ticket fixes could easily solve open source developer burnout.
Allowing redistribution and commercial use
The biggest Achilles heel of open source is allowing redistribution of software as opposed to merely source available software available for private use. There are too many freeloaders on open source. It is also deeply unethical for someone else to make money out of your free contributions. Plenty of open source contributors are screwed over here when project owners get investor funding and contributors don’t see any of it. Github also did this cleverly by associating itself with words like open and community but never really had open source. This is nothing short of fraudulent. Open source developers need to understand contributor agreements before they commit a good chunk of time to work on open source. Money flows need to be transparent in open source.