This is mostly regarding software. . .I’ll go first:
Not seeing pricing until you give a company your email. (not naming names).
Needing a code to enroll on said company’s list and the email comes after you’ve moved on to two other projects.
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When I run into something like this, I have a two step solution:
- Search Google for a review that mentions pricing. If unsuccessful,
- Find another company.
If you don’t hear the name of the “give us your email” company at least once a month on CNBC, they aren’t unique. (IMO)
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When your password autofills wrong. I just had my TOTP code go into username.
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Lots of professional software you have to “ask for a quote”. And then there are annual “maintenance” fees.
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Likewise, being forced to “start a free trial” before they reveal the pricing.
I follow @WayneG’s advice re: Google, and you can sometimes find pricing if you append /pricing to the URL, or scrounge around in the footer of the website.
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Or, not remembering where the password is stored (If you’re using both the Apple app and 1password). The former is very convenient but I’m also using 1P for now.
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When I tap to position the insertion point when editing text on my iPhone or iPad, and it selects whole words (or multiple words) instead.
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OTPs getting filled wrong - I have SMS sync with messages and quiet like the feature where safari auto picks up the OTP from messages. Starting with Sequoia at random times the OTPs get filled up wrong on bank website which is quiet annoying
I haven’t used capterra.com since I retired, and it took a while for me to remember its name. 
But it was one site I used from time to time. A more recent find is toolfinder.co.
Anything that allows creating smart lists or groups and doesn’t include a Create Date and Update Date as options to use.
Password fields that don’t allow pasting. Actually any field but passwords bother me the most because they are really hard to type.
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I have StopTheMadness Pro, and can paste into most, if not all, password fields. I think it’s this app that allows it. But I’m not 100% sure. I have it running on all my devices and don’t have a problem with password fields.
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