It’d depend on your budget. It seems like anonymity is a top priority for you, so I think prioritizing a “private” Android OS like GrapheneOS might be preferable to choosing a cheap Android phone that will provide security updates for a longer period of time. I believe the Pixel 6 is only guaranteed full updates until October 2026. That being said, it looks like GrapheneOS provides OS security updates for some EOL devices going as far back to the Pixel 4. EOL devices will lack firmware and driver security updates, but OS updates alone might be good enough.
At the end of the day, it’s really hard to say because it depends on what you want to prioritize while also keeping to your budget. If I were in your shoes, I’d probably pick the newest Pixel I can afford and get GrapheneOS. If you’re on a really tight budget, see if you could afford a 6a rather than the 6 since it’ll last you almost an extra year. I’d definitely recommend avoiding option D if you can help it.
I’m not familiar with the privacy implications of eSIM vs SIM specifically, but there are a few things to keep in mind depending on how serious you are about remaining anonymous. You didn’t go into your threat model so I’ll just list a few things to consider and you can decide how far you wanna take it.
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For maximum anonymity, you should avoid SIM/eSIM entirely. But if you want to use this phone while you’re out and about, that’s probably not practical.
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If you need a SIM/eSIM, it’s best to acquire a pre-paid plan anonymously. So long as your country doesn’t require that you identify yourself, you should be able to get a pre-paid plan in cash without providing any real information.
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If you’re going the “anonymous pre-paid plan route”, you should know that giving out the phone number tied to your phone can easily de-anonymize you. Michael Bazzell goes more in-depth on this if you can manage to find his now deleted podcasts which probably have some outdated info. For the sake of time, I’ll skip the explanation and just advise you to never give out the number that is used on your phone from your pre-paid plan, only use it for mobile data if anonymity is a serious concern. If you need to use a phone number, use a VoIP service. JMP is a popular choice among privacy-conscious people, if I recall correctly it is because they support anonymous signup and payment methods.
If you just want to protect your traffic from your ISP, using a decent VPN service 24/7 should help.
I think you pretty much nailed it. The best option is to enable airplane mode and put it in a faraday bag when not in use or when at home. If you must use your device at home, the next best thing you can do is disable mobile data and only re-enable it when you’re away from home.
If you need to use apps that require Google Play, GrapheneOS already sandboxes it. If you’re using “Googled Android”, a VPN or DNS service will be quite limited in protecting you from Google. I also can’t speak to the efficacy of Beeper, but I’d advise that you avoid it for private messengers like Signal. It might have a use for privacy-invasive messengers, but that’d need to be a separate discussion.