I would go for the Mediator.
The problem with the X-Surf100 + RapidRoad combo is that it still has unsolved technical issues. With a Mediator, the expansion possibilities are even wider, and you could even sell that Picasso IV to fund the entire Mediator setup.
I was thinking the same thing about selling the Picasso IV to fund a Mediator but there are advantages and disadvantages.
Mediator advantages/disadvantages+ Voodoo3-5 or Radeon gfx boards are more than 2x as fast at 2D than the Picasso IV
+ Voodoo3-5 has 3D
+ gfx card memory can be added to Amiga fast memory
+ good and cheap PCI gfx, ethernet and USB boards are possible
- Elbox sells overpriced Spider where generic USB PCI cards are cheap
- separate gfx card monitor output from Amiga
- no scan doubling/deinterlacing/flicker fixing or pass through of Amiga native modes
If not using native Amiga modes much and wanting to play with 3D, then the Mediator is a good choice. It is too bad that Elbox's greed with the Spider makes the Mediator setup so much less appealing. I bet they would make *more* money if they supported generic PCI USB cards and had a better reputation.