Android

Yes, bloatware can be disabled easily with Universal Android Debloat

Samsung galaxy A15 5G, Cheap phone (~180$), micro-sd, headphone jack, good software support (4 OS updates, 5 years security updates), good battery, 1080p amoled 90Hz 800 nits.

I think the Pixel line is great if you don’t like bloat, and they offer you lots of flexibility because you can replace the entire operating system without the hardware fighting you every step of the way. They are intended to be excellent development phones, and the aftermarket rims on these devices are very stable and well-maintained because they benefit from Google’s investment in maintaining the reference images.

The Pixel I had developed an issue where it didn’t maintain a stable cellular connection, but I still love the product line.

I do sense some conflict in your requirements, however. One man’s “fun feature” is another man’s bloat. I’m not saying that your process is flawed, rather, that it’s a very personal decision.

How about a ruggedized industrial Android phone?

Cat S42 H+

Has:

• 3.5mm jack
• microSD card slot
• IP68
• MIL SPEC 810H
• Dual SIM

I see price on Amazon US is $168

If you want really fancy features, the higher end model has a FLIR thermal camera built into it.

Fairphone 5 stands alone as the phone that is most built to last. Its repairability rating on iFixIt is a perfect 10. They've committed to software updates until 2031.

Not sold in the US, unfortunately, but I think it has the correct 4G/5G bands for US networks if you want to import it.

You might also be interested in iFixIt's repairability overview here: https://www.ifixit.com/repairability/smartphone-scores#smartphone-scores

In Canada, probably a Pixel 8. You can find new ones for cheaper on Marketplace. The upcoming 8a might be a good deal too.

I have Fairphone 5 and it's not bad. Little bit pricey and no wireless charging or headphone jack but it should last really long with spare parts for years and easy fix.

If you need a phone that last long you should get a base varient of Samsung S23/S24 with 256GB storage. It checks most of your boxes but the main reason for suggesting Samsung is the repair parts availability after 5+ years also getting a repair outside warranty won't cost you a fortune. Just debloat it and you are good to go until you hard reset.

I might give GrapheneOS a try

You definitely should. It's pretty wonderful imo.

Missing some of the stuff you want, but I'd also recommend the Pixel+GrapheneOS. The Graphene web installation is ridiculously easy and it's rock solid in my experience. You get 7+ years of support from Graphene too. Pixel build quality is great. Great camera, solid storage (ymmv), plenty of RAM. In my experience, Google's hardware support is really good. I've been using their phones since the Galaxy Nexus and any time I've had even a minor issue they're just like, "it's under warranty, do you want a new one?" basically no questions asked. My Pixel 6 is two years out of warranty. A few days ago the battery started to swell a bit. Reported it Sunday and I have a free replacement arriving today. All they asked for was a pic and my mailing address.

Last summer, my nephew managed to grab my phone, take it out of its case, and drop it in the street where it was run over by an SUV. The only damage it took was some serious scratches on the back glass. My old Pixel 3 survived two years in my pocket working on an organic farm and it's still kicking as my temporary replacement. I've found their phones shockingly durable.

The death of almost all my phones has been the phone carriers withdrawing support for the phone modems. 2G to 3G to half-assed LTE, so I finally got a relatively cheap 5G phone and that will hopefully do me for a while. That said, the LTE phone (Moto 4G) lasted 5+ years before it became near unusable, again because of carrier support, but also because web bloat had slowed the browser to a crawl.

I think, basically, that you can get sufficiently good phones pretty cheap now, and it's not worth spending $500 on a 4 year phone when you can spend $150 each on two 2-year phones. Beyond 4 years I think you can't count on anything.

I've been using Moto G series if that matters. The hardware value for money is very good, almost everyone agrees. They have notoriously short lived software support. I don't know how much I care. My G4 that I got in 2017 was still running Android 7 when I retired it late last year. I might attempt to run LineageOS on it, but really, the thing is slow and the hardware (Micro USB port and volume buttons basically) are now flaky, and again there is the carrier support issue, so it's basically not worth it.

See: https://www.motorola.com/us/smartphones-moto-g-family

The most interesting ones imho are the 2023 G Stylus 5G (the one I have, $250), or the 2024 G Play or 2023 G Stylus (4G) (both are $129). All of these run Android 13 and will supposedly get an upgrade to 14. There are also some new models with 14 already, that cost a bit more. All have microSD slots except for the 2024 G play. All have headphone jacks and I consider that important. I think some of the new ones might have wireless charging, but otoh I think that may make it harder to replace the battery.

I have been using a galaxy s21 for almost 3 years with nova launcher. Still works perfect other than the battery not holding charge as long .

Currently I buy a 100ish bucks Chinese smartphone around every 2 years and I sell locally the previous for around 2/3 of the original value, if you bought it from overseas sometimes you still recover 100% of the value after the 2 years of use.

So my advice will be buying a 150-200 bucks phone overseas and do like me sell it locally after the 2 years of use and then buy another 150-200 bucks again.

I buy 100ish cos it's enough to run my online business but if you need something better it's up to you.

The key it's into buying it directly from China just be advised of the tax local regulations, if you keep the budget you can eventually didn't pay any tax.

Good luck.

Edit: my point it's it didn't matter which phone you will buy what actually matters it's to juice it for two years and then resell it and recover a good amount of the original value, that way if you make more money with it basically you will pay nothing for the phone.