I've had the older Fluke 8840A, which was the precursor to the 45, which was the precursor to the 8808A. It was a real beast, mechanically. Beautifully made. I noticed the 8808A is made in China now, so I'm not sure the build quality would be the same. The 8846A is made in USA still.
I have the 289 "handheld" meter. It is a great meter, but it will probably not leave your benchtop because it is HUGE and HEAVY. If that is OK, then I think you would like it. Mine has stayed in spec (as far as I can tell) for a couple of years without calibration. I think the best feature is event (changes in the reading, rather than recording at timed intervals) logging and being able to look at the result on the meter. No need to mess with a PC. However, note that you can't view a live graph of the data as its being logged. One other drawback besides the size is the high resolution display. I find a standard segmented LCD easier to read (and VFD even easier). That said, with all of the features available on the 289, the hi-res screen allows for menu selection which is very intuitive. Fluke leads (made by Pomona) are top quality. Fluke charges an arm and a leg for their PC Flukeview Forms software and USB cable, so if you're interested in getting that, I would buy the package with the meter and the cable/software included.
If you are referring to the U1253A/B OLED meter as Agilent's top one, I don't have that meter but I do have the non-OLED version (U1252A) which is otherwise essentially the same. The user interface with the small, strangely placed buttons is weird to me, compared to Fluke's layout. I think the fast update speed of the display is supposed to be a feature, but I find the rapidly-changing numbers more of a distraction. It seems to be very accurate, but I haven't had mine long enough to say anything about long-term stability. The test leads/clips that it comes with are decent quality, but are not in the same league as Pomona. Agilent gives their PC software for the meter away free. I assume you've seen Dave's video review of this meter.
Regarding the Agilent bench meters, I have no firsthand experience with any of them, but I have been looking at them, too. If you are going to spend the money for a 34401A, the 34410A is not much more money for a much more modern meter. It has USB and a dual display, as well as advanced logging features. It also has capacitance and temperature, which the 01A doesn't have. I don't see a good reason to get the 34401A unless you need to be consistent with other equipment you already have.