[Jtsummers]

Whoever makes that paid software has to compete with the free software. Which means that customers end up with a choice: crap, but works well enough and is free, quality that works well but costs $50-500. The various mobile app stores have produced a pretty effective demonstration that people (as a general rule) will happily accept garbage apps for $0 or $0.99 or 2 minutes of ads for every 30 seconds of use rather than paying even $5 for better software.

I'm willing to pay, and you're willing to pay, but are enough people willing to pay to support better systems?

[sirmarksalot]

I think companies are generally willing to pay money for software, but the things they're willing to pay money for are generally not the things that would make their employees' lives easier. Employees value reliability, ease of use, and speed, while the companies themselves value integration with other systems and ISO compliance.

Atlassian software is not good, and it is not cheap, but it does offer an end-to-end story for the rigid workflows encouraged by many investors.

[Wowfunhappy]

I'm not arguing you're wrong, but I'd like to harp on one point:

> The various mobile app stores have produced a pretty effective demonstration that people (as a general rule) will happily accept garbage apps for $0 or $0.99 or 2 minutes of ads for every 30 seconds of use rather than paying even $5 for better software.

Those stores have also been set up in such a way that buying expensive software doesn't make any sense. I'm not super familiar with the Play Store, but at least in the App Store:

1. Developers can't offer free trials, so I have no way to test out an app and see if it's worth $$$$$.

2. Developers can't offer upgrade pricing, so I may have to pay the full entry price again in a couple of years, particularly because...

3. Apple's yearly OS updates break or create bugs in existing apps all the time, which means no amount of up-front developer testing can ensure a truly stable or long-lasting end product. These iOS updates are required to continue receiving security patches, and if I upgrade and discover a critical app broke, downgrading is impossible in almost all cases.

So yes, I almost never pay more than $5 for anything in the App Store, because the ecosystem is built to ensure anything else is a bad investment.

[Jtsummers]

> 1. Developers can't offer free trials, so I have no way to test out an app and see if it's worth $$$$$.

Yes they can. Via in app purchases, they can offer a reduced set of features for free, and the full set for money. As an example, I have Working Copy (free) but have (twice now) done the in app purchase to unlock "pro" features because I've found enough utility in the software. It will work without the purchase, though, and is perfectly fine (no one, in person, that I've recommended it to has ever paid for it, but still use it).

> 2. Developers can't offer upgrade pricing, so I may have to pay the full entry price again in a couple of years, particularly because...

At least some have worked this out. Buying OmniFocus 3 (?) with OmniFocus 2 (?) still installed on your device got you a discounted price. I'm pretty sure that Scrivener did the same, but don't quote me on that. I purchased it a long time ago.

> 3. Apple's yearly OS updates break or create bugs in existing apps all the time, which means no amount of up-front developer testing can ensure a truly stable or long-lasting end product. These iOS updates are required to continue receiving security patches, and if I upgrade and discover a critical app broke, downgrading is impossible in almost all cases.

That I can't disagree with.

[Wowfunhappy]

In app purchases are a handy workaround, but they necessitate that the developer offer a usable free version per Apple rules (which they don't always apply entirely consistently). My understanding is that you can't have the app entirely shut down after X days without payment, so developers need to spend time creating some level of freemium functionality.

That's certainly doable, but it's more work, and you can see how the system has been designed to push you towards a specific pricing model.

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Aside:

> At least some have worked this out. Buying OmniFocus 3 (?) with OmniFocus 2 (?) still installed on your device got you a discounted price.

That's a really clever way to do it!