LTK is a better film than DAD but it underperformed and was - perhaps unfairly - viewed as a flop, whereas DAD made loads at the box office.I think Licence to Kill is the best of all the Bonds' final films, I guess they didn't know it is was his final films when they made it mind you.
Not sure if they'd decided DAD would be Brosnan's last film until after it was made
Most trade magazines and fans expected Pierce to return (as did he). As to why he didn’t, I’ve heard that he wanted too much money and priced himself out, but there was also the fact of Bourne and the like, which supposedly made Barbara feel that 007 needed a move away from invisible cars etc, despite DAD’s financial success.
My recollection from the time is that as soon as LTK’s box office returns came in, the press were speculating about Tim’s future and blood was in the water. Whether he may have returned had various legal issues not paused the franchise for 6 years (no longer as big a deal as it was at a time where 007 films came out every other year), well, we can only speculate.
So as to who went out on a higher note, the guy with a solid but underperforming movie or the guy with a widely-ridiculed but financially successful one, well, as one of my old lecturers used to say, you pays your money and you takes your choice.