Since you’re new, I recommend searching for similar posts and requests for answers harder. It’s all here and on the recommendations page on the main Privacy Guides website.
Also since you’re new, I recommend catching up on videos by Privacy Guides and Techlore. They are very easy to understand and teach you a lot about what, why, & how about the privacy space.
There are hardening guides, tips & tricks videos out there to find tune your OS for optimal privacy & security without loss of significant convenience. I suggest you continue researching, reading, watching, trying, and learning.
I suggest you also check out IVPN if you’re amenable to trying another option. Its kill switch enables before even the GUI loads on macOS (as I understand).
I think its actually better that your email/username doesn’t include any PII. Use anything you want as your email. This is a non issue so don’t think too much about it. I know this is contrarian advice but I hope you’ll come to see it as you continue in your privacy journey.
It’s not terrible but highly functional only. I know it looks boring to folks always used to shiny new UI/UXs all the time but it does its job really well. If encrypted email service is needed, Proton and Tuta are great! If encryption is not needed, I suggest checking out Fastmail. It has the UI/UX you’re likely looking for.
iMessage is not bad. You can change your settings such that you only receive and send iMessage via your email so you don’t always have to keep giving out your phone number to use iMessage.
Signal should be used as much as possible. And it also has usernames so you don’t necessarily have to share your phone number here either.
Fingerprinting is complicated and nuanced. If anti fingerprinting is what you want, Mullvad Browser is for you. Albeit, hardened Firefox or Brave browser also work really well. Follow Privacy Guides recommendations here for starters.
Brave Search is another option I suggest at-least checking out. Albeit, I am currently persoanlly using Kagi myself and am liking it. I seldom have to search Google unless I am doing a deep dive on a topic which is not often.
duck.ai and NanoGPT are the best options for Gen AI use. You should know that using AI is inherently a privacy invasive tool so be sure to never share any PII in your searches. I highly suggest NanoGPT because it is a pay as you go model, no subscriptions if you don’t want it and you can use literally any AI model you want. Plus, you can access, pay, use it as privately and anonymously as you want.
Simplelogin is great and so is what’s built in Proton Pass. That’s what I use. But there are other options you can check out to see what you like best before picking one for long term use. Duck, Addy.io, AliasVault (beta) are all decent options too.
Proton Calendar is great! And so is Tuta’s calendar. But if you want to be able to use calendar on any platform, I suggest checking out Posteo’s encrypted calendar service that you can use with CalDAV anywhere you want.
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I have also given many similar answers on many posts here including this one recently. So, check this big thread out to learn more. Looking for a Practical Long‑Term Privacy Stack (Proton, AI, VPNs, Photos, etc.)
Hope this addresses your questions. Again, since you’re new, a lot of reading, researching, understanding, and trying is likely needed to learn what many here know.
And welcome to the forum! And feel free to ask follow up questions should you have any. That’s another way to keep learning.