Nice soapbox.
Now here's what can happen.
TL;DR:
1) It just works. iPhone.
2) "I don't mind putting in some research and the community is more reliable!" Android phone that meets requirements.
3) Windows Phone is unproven with Windows 10 Mobile. WP7 and WP8.1 breaks leave bitter taste.
4) Used phone.
5) Reduce expectations and live with an older phone as-is.
6) Go dumb.
iPhones are supported the longest in general with now, a five year expectancy. It think five years is reasonable personally and this is the gold standard. Physical repairability for these generally is on the poorer side but parts are abundant.
In Android land support ranges from nonexistent to the Nexus phones which standardized on two years of guaranteed feature updates IIRC (unacceptable to me) with an extra year of security updates. (I say guaranteed because Google can and does release some updates beyond that two year thing but doesn't guarantee it.) Most manufacturers aren't as fast and consistent for as long but luckily...
On the other hand, many Android phones, depending on the model, popularity, etc. have an active custom ROM scene which can extend the useful life and add features for a pretty darn long time. This may be your best bet at staying somewhat up-to-date for over five years.
Even if ROMs somehow all stop you'll still have Google Play Services updates and stuff to stand on for a bit. (Since Android updates are often iffy across manufacturers, Google tries to keep older versions in the loop for a bit.)
In this case, the phone's inherent hardware like RAM will likely become the limiting factor which is probably more your taste.
Physical repairability varies here, with some phones like the Nexus 5 being easy to repair and some being relative nightmares. (cough Galaxy S 6 and its sandwich of glue cough) So that may be a factor too. Check out iFixit and it's repair scores.
You can get a used phone too. Great choice if you're worried about lining someone evil exec's pockets. Helps keep yours lined too.
You can curb expectations.
I made an aforementioned Pre 2 with webOS my daily driver for a bit last year and it technically worked fine for the basics. Just not the advanced smartphone services and stuff that's come out since.
It has no voice assistant or apps like Uber and Snapchat, but it still works and met my needs. I didn't NEED the extra modern bells-and-whistles, they're just nice to have.
We have more access under-the-hood than WP7 and can fix sync behavior and stuff if necessary. But the web browser is still meh at best, etc.
On the extreme end we have a Treo 650. The model itself is just over a decade old and it is prehistoric. It would not have been practical to keep this up-to-date for 5 years, let alone 10 because hardware. (why I hold 5 years today as more reasonable) I think we've hit the point of phone spec requirements leveling out a year or two after the 900 launched actually. (making 5 year support more practical)
I can do texts on that Treo but MMS is iffy. Phone calls and the basic PIM and apps work, but only 2G connectivity. Email? Nope that's broken. Palm OS was discontinued 4-5 years after this launched and Palm has since dissolved a couple years after that. Much closer to a feature phone today.
Also might want to poke your head into XDA's WP7 section. There may be some hacks and stuff you can use a la webOS and Android since some people did get under the hood of WP7.
And when you say reset, I'm going to assume erasing the phone and not suggest that.