While I agree part of that was being that there were fewer options, there's also just more complexity these days.
I consider things like:
* Does this synchronize to other devices?
* Does this support the device(s)/OS(es) I want to use it on?
* Does this integrate to other applications I use?
* Is this likely to contain malware, or could it in the future?
* Does it require me running my own infrastructure, or can I pay someone else?
* Am I comfortable with the extent I'll be locked into this ecosystem, if any?
* Is it a worthwhile cost to me? Is the price likely to radically change in the future (after I'm locked in)?
* If free, why? (Am I the product? Are there or will there be ads?)
* If open source, is it likely to stay that way? Is there a community around it? Am I capable of maintaining this if I need to?
* What new security threats does this open me up to?
Granted, I don't always care about all of these (sometimes depending on answers to others), but it's a way bigger list than I'd have had 20 years ago.
I consider things like:
* Does this synchronize to other devices?
* Does this support the device(s)/OS(es) I want to use it on?
* Does this integrate to other applications I use?
* Is this likely to contain malware, or could it in the future?
* Does it require me running my own infrastructure, or can I pay someone else?
* Am I comfortable with the extent I'll be locked into this ecosystem, if any?
* Is it a worthwhile cost to me? Is the price likely to radically change in the future (after I'm locked in)?
* If free, why? (Am I the product? Are there or will there be ads?)
* If open source, is it likely to stay that way? Is there a community around it? Am I capable of maintaining this if I need to?
* What new security threats does this open me up to?
Granted, I don't always care about all of these (sometimes depending on answers to others), but it's a way bigger list than I'd have had 20 years ago.