I don't have the technical know-how to do this - but i am reminded of the nay-sayers regarding Majsta's FPGA pursuits. They said it couldn't be done - yet he persevered and he proved them wrong. Someone who has the desire , enough time , money and will power to give this a shot!
Who said it couldn't be done? I don't know anyone that he has proved wrong.
Using a raspberry pi to respond to 68000 bus cycles using gpio is pretty crazy. I won't say it can't be done, but any result will probably not work very well. Those IO Pi Plus 32 channels are connected to i2c, I don't think desire/time/money/will power will cut it. You could stick a bridge between the amiga and the pi, which may as well be Ethernet. It would be pretty cheap to make an a500 PIO Ethernet adapter, a DMA one would be preferable and likely more costly.
What irks me is that a quad core 1.2Ghz ARM Pi3 with 1GB ram, 6 USB ports, serial I/O, Bluetooth, Wi-Fi, microSD slot, Ethernet and HDMI output and can run Kodi costs $35 but we can't create a 100Mhz Amiga for less than $500....
Are you kidding me?
If you could create an amiga that was as cheap to manufacture as a raspberry pi and would also sell the five million the raspberry pi has sold. Then you could get one for $35 dollars. The raspberry pi is just an existing chip put on a board though, so the development cost was low. Therefore you'd need to figure out how to get someone to design all the chips and masks for free.
Give me a billion dollars and I'll build you a 1ghz $35 dollar amiga which would be the same as a PI but feature 68060 and SAGA. If you want an actual computer you may want pci express and possibly pci/zorro (although those may be better suited as external bridges).