rattrattus I'm still researching which to go with, but if I find one with a headphone jack I'm willing to take whatever.
Yeah unfortunately all the pixel devices with tensor chip don't have a headphone jack. I don't believe the marketing around that (more space in the phone, better waterproofing, "COURAGE" :D) because in the end by far the most important reasons are related to revenue, and all phone manufacturers happily sell you their premium Bluetooth TWS Earbuds with the new jackless phone (apple even makes much more money by licensing their proprietary lightning port). Interestingly many of the cheap phones nowadays offer headphone jacks alongside expandable storage, great water resistance and battery life. Guess the premium brands just forgot how to manufacture quality devices, but okay I finish my rant. USB-C adapters or headphones will be the thing to use if you don't want to do Bluetooth.
And yes, please take it easy and one step at a time until you are living your very personal privacy dream. Using GOS is a huge step towards better security and privacy, even if you don't change anything else at first. It took me almost 3 years and 4 devices with GOS and now I feel like I finally got my perfectly clean setup on the Pixel Tablet, so probably from here on I know what to do with whatever comes next. The only thing I regret is not signing up here earlier in the process, this community rocks and will help you find the best approaches to whatever problem you face.