Agree 100%. And sometimes, horror of horrors, one realizes that one’s time is more valuably expended on doing one’s work than constantly fidgeting with “new and better” apps. 
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Well said, will give that some thought.<<
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Note mind you that I have not achieved perfect contentment! 
I’m a work in process; my wife thinks I’m too slow when she gets the Amazon bill.
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Aren’t we all? 
(20 characters yadda yadda yadda)
Love the yadda, I’ll use that next time I need those 20 characters!
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IMHO, most people think about this way too hard. The only relevant question is, taking all factors into consideration including costs, does an app do what you want and need it to do? If yes, then you are done, move on with your life and work, don’t waste time and brainpower thinking about it further. If no, find something else. It’s not rocket science.
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Personally, I prefer (and happily pay for) specialized third-party software or services wherever possible, esp. if that product is the company’s major product (e.g., BusyCal vs. iCal, or Arq vs. Time Machine/iCloud backups). From my limited experience, this gives a much greater chance of app longevity & reliability of service which is important to me. W.r.t. Apple, you never know if/when Apple shifts its priorities and leaves a product or service unsupported (I’m still burned by the loss of Aperture).
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Tooling is a rabbit hole you can go down as deep as you want or need. It’s a lot like coffee gear.
You can make a decent cup of coffee with some pre-ground coffee and a drip coffee maker…
…or you can get a blade grinder and a Chemex and make better coffee.
…or you get an expensive conical burr grinder, a scale, a fancy espresso machine, and a kettle with an adjustable temperature setting, and learn all the specifics of brewing the best coffee you can.
Apple’s tools are good enough for most people and most use cases. For those of us who want to go much deeper and seek master-level productivity, you’re going to run into roadblocks or features you need to get to the next level.
If Apple’s tools are sufficient for you, use them. If not, seek an alternative. There’s no best route, just varying levels of depth and complexity to explore.
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Well said. As one who used to evaluate software for my users, as well as myself, I can tell you that rabbit hole is very deep and the entry price can be expensive.
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I’m generally cool with that, until I find out the tool doesn’t do that one thing, then I start looking for something that does, and next thing you know you’ve cycled back through 5 task managers and 3 note systems 
If you’re cycling through that many apps it seems more than “one thing”.
Ultimately I’m a satisficer, and with some exceptions (I just can’t use some apps if they limit one to specific embedded fonts I dislike) I make a choice then do what I can to best get along with it … until it’s no longer tenable or some well established app is decidedly better . Too many people are dilettantes and make themselves unhappy when they should be aiming for satisficing their needs. Searching for the chimera of task manager or note perfection is a trap.
I think sometimes the “cycling” has to do with trying to solve an immediate need you have, finding an app that solves that need, and then realizing that the new app doesn’t do something that you took for granted.
It’s helpful to try to brainstorm everything you need the app to do and not even evaluate apps that solve one problem but create another - or at least to be aware of the tradeoff when you’re looking at app alternatives.
Trying new things doesn’t necessarily make me unhappy. It’s exciting to see new things. I am definitely a maximizer according to that article.
For sure, however when a company comes out with a new feature that someone has been waiting for it’s really easy to look again. For example, when Apple Notes got the immediate note function from the lock screen, I looked at moving towards that instead of Evernote. I wanted it to work because at first glance it was worth a try. However, shareable notes and web access ended up being more important.
I think sometimes I can’t conceptualize what is good or bad until I experience the pain points in my day to day. And to quell people’s disgust at the App tour de france, I have been happily committed to Things and Evernote for the past 6 months of my life. 
lol
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Cycling through numerous apps to do ‘that one thing’ may make you happy but I doubt it does for most.