I'm tempted to try this on our Model Y. On our older Model S cars this linking profiles to fobs was a mess and never worked right. It almost always switched to my wife's profile as I was getting in and cramming me against the steering wheel. I am a bit concerned about the constant relocating of the seat and it's wear and tear on the motors long-term but it may be worth it in the short term in the way of improved user experience every time.
My wife has easy entry on, on her profile, and I dont, on mine. Like a lot of other people my wife and I are pretty different in height. She is 5' 6 and I am 6' 3. My driving seat position is not very different than the easy entry position we have setup for her.
Anyway, I have found that linking the keys to the profile works well, with the caveat that I said previously. We both have our phones setup as keys, and in order for it to work properly "most" of the time (like high 90%), the person who is going to drive the car should open the drivers door, before the other person opens the passenger door. We keep the car locked in the garage though, and I am not sure if this is related to that.
It will still "mostly" work if the passenger opens the car door (unlock the car) first, but it seems to reliably work if the driver opens the car door first.
The workflow that we sort of unconsciously developed is, because we have a home alarm system we set when we go out, the person who is driving goes to the garage to get in the car, and the other person turns on the home alarm, then comes to the garage and gets in the car. This slight lag time (turning on the alarm) is enough for the person driving to naturally get out to the garage and open the door without rushing, or waiting.
When we go out to dinner or something, and go out to the car to go home, its a bit less reliable and I think thats because I still open the passenger car door for her when we go out.
Anyway, TL ; DR , I think it works pretty good, I dont think easy entry is a requirement (although it helps if you are different heights so the car isnt on the shorter persons height), and having the driver be present, on the drivers side of the car and opening the locked door before the passenger with their own phone key opens the passenger door seems to matter, but thats anecdotal.