Looking for insight on two watches

[Mainewatchman]

Between the AP 15400 RO on strap white dial (I own) and the Day Date yellow gold with silver diagonal motif dial. I have owned a couple Rolex and they haven't really done much for me but this would be my first Day Date, which I have always loved.

I have trimmed my current collection down to:
AP 15400 RO on strap (dress watch)
AP Chrono panda (weekends)
Omega Aqua Terra (daily)

I would need and want to move a watch to get the Day Date and I can't decide if I will regret this. My last couple purchases have been AP, which I have loved. Going to Rolex a bad move even if it is the Day Date? My thought is that the Day Date will serve the same purpose as the 15400 and at this time it is getting the least amount of wrist time. So I am hopping that someone that has owned both of these or either of these can give me some pros and cons to the watches and if they could select one now what would it be? Appreciate any insight!