p1xel_p0etry I bought the Pixel 10 from a retailer in cash without sharing any info, in person. On the phone, I skipped through the setup to get through without provided any info. I have not inserted any sim card or turned on wifi or BT even once.
As Probably9857 said, IMEI is still recorded by cell towers even without a SIM. See https://discuss.grapheneos.org/d/2509-are-cell-identifiers-leaked-on-first-android-boot-before-installing-grapheneos. More discussions:
https://discuss.grapheneos.org/d/9874-is-phone-trackable-without-a-sim-card
https://discuss.grapheneos.org/d/19535-does-imei-get-sent-to-towers-on-gos-without-a-sim
There is unconfirmed speculation that there could be a small amount of Bluetooth radio activity at during boot for both stock Android and GrapheneOS. If this is true, it's unclear what this activity is and what identifiers are involved. See https://discuss.grapheneos.org/d/26586-brief-note-on-mobile-phone-measurements-with-airplane-mode-onoff and https://github.com/GrapheneOS/os-issue-tracker/issues/6469.
p1xel_p0etry My understanding is that first per-requisite to installing GrapheneOS is to update the phone.
While recommended as a best practice, this is not required. From the Web installer guide:
It's best practice to update the device before installing GrapheneOS to have the latest firmware for connecting the device to the computer and performing the early flashing process. Either way, GrapheneOS flashes the latest firmware early in the installation process.
The Pixel 6a is the only phone that requires an update before installation, as documented later in that same guide:
For the Pixel 6a, OEM unlocking won't work with the version of the stock OS from the factory. You need to update it to the June 2022 release or later via an over-the-air update. After you've updated it you'll also need to factory reset the device to fix OEM unlocking.
A stock OS update can take a long time to install, especially if downloading over a slow connection. I never updated the stock OS and I haven't had issues installing GrapheneOS on a new Pixel device. Stock OS collects telemetry data, so you may want to minimize how long the stock OS is running.
p1xel_p0etry Add a client to my Pixel by transferring an APK from my laptop to the phone via cable. I don't think this would work as I can't turn on the VPN until I login which would require internet. I could be wrong about this.
You're going to need to connect some device to the phone to ultimately perform the installation. Both stock Android and operating systems such as Windows collect lots of telemetry. It's possible that USB identifiers from your computer or phone are collected by the other and stored remotely. That's something to be aware of if this is a concern. See https://discuss.grapheneos.org/d/27314-privacy-risk-of-booting-on-an-idd-device. If using a laptop, booting a live Linux distro is an option.
p1xel_p0etry Also, my big assumption is that I can download the update my phone on VPN, please correct me if that's not possible. I haven't used an Android as primary phone in 12 years.
I haven't heard of issues with downloading stock OS updates on a VPN.
p1xel_p0etry I am considering doing this at a coffee shop just to be safe, maybe a Starbucks wifi would likely be reliable enough.
Starbucks Wi-Fi typically requires a name, e-mail, etc. to connect. You can provide alias information, but be aware of what you provide and how it is associated to you if this is a concern.
p1xel_p0etry Let me know if there is a step during I should be careful about.
The Web installer requires you to download the GrapheneOS image, which is almost 2 GB. The installation image cannot be downloaded ahead of time with the Web installer. The download will take a long time from a slow internet connection. If using public Wi-Fi, you may want to speed test the network ahead of time so you're not stuck in the middle of an installation waiting for hours to download the file. It is possible to download the image ahead of time with the CLI installer, but the Web installer is much easier to use.
p1xel_p0etry Once GrapheneOS is installed.
Once GrapheneOS is installed, it will boot with factory settings with airplane mode off. This means the phone will connect to cell towers again until airplane mode is enabled.
p1xel_p0etry disable OEM Unlocking in developer options
This step is now integrated into the initial setup during installation: https://grapheneos.org/install/web#disabling-oem-unlocking. This no longer needs to be done through Developer Options.
p1xel_p0etry My day to day will be using my pixel 10 offline or using wifi to connect to my portable hotspot device with VPN especially when I go out.
A portable hotspot device has an IMEI and will allow tracking of your location. I'm sure you're aware of that, but it's unclear what you gain by using a portable hotspot instead of a data SIM in your GrapheneOS phone.