I'm sure I cannot add much of technical value to the discussion, compared to other experts here, but just commenting that I opted for the 8588A in my small accredited lab, and I find them to be excellent from a useability and breadth of capability perspective.
I actually purchased two of them, with external calibrations occuring in alternating cycles so that I can perform cross-checks and continue running with one while the other is away for calibration. I only have a couple of years history (back to Fluke UK each time), so it's hard to draw strong conclusions on stability, but so far the stability on all functions has been good against the 1 year specification, so I am confident that true performance is well within my uncertainty budgets.
I have used and had always intended to purchase the much-loved 3458A when developing my electrical capability, but in the end I assessed that the configuration of the 8588A ranges and extra capabilities might be better for my application. I certainly have no complaints from my experience with the 3458A, and although not well founded in real data, my understanding is that the 3458A might be the ultimate instrument if you are very strongly focussed on DCV linearity. It's difficult to get specific linearity specs for the 8588A to compare, but in my case the absolute accuracy spec of the 8588A DCV (including non-linearity, temperature and 1 year drift) was still substantially better than I required.
I don't usually use the 30A range on the 8588A (I prefer to use an external shunt instead), however one of the well regarding reference labs in Australia has commented to me that the 30A range in the 8588A is significantly better than the 20A range in the 8508A in their experience, most likely due to the addition of active cooling.
Although it's only simple, I do like the external shunt feature on the 8588A - I have them programmed with all of my DC shunts and find it very handy to take readings directly in current units.
A dissapointment for me is the limited range (with 10% only) in which the transfer spec is used for ratio measurements. This has already been discussed here and in other threads, and is a significant impediment to using the 8588A to transfer traceability between standards of different values (i.e. across decades) and perhaps hints at a lower confidence from Fluke in the linearity over a full range.