Good news -- I just went back to removing the bottoms of the sockets and doing the soldering the "normal" way. Unfortunately sometimes the socket bottoms come out intact, and sometimes they are destroyed.

So sorry, it's just not viable to put them back in afterward

But the GOOD news is my SIMM worked on the FIRST try with NO shorts at all. So basically it's 300 times easier to assemble the board when you cut the bottom of the socket out. I'll keep doing it that way since it's more reliable, at least until I can try to bake the boards with some reflow soldering.
It was mostly the fact of an existing driver to treat ROM space as a read-only Mac drive that I wanted to point and wave at

The SD card thing was purely an afterthought.
Gotcha...yeah, we'll have to look at the Mac Classic and see how it does it. It would be GREAT if the driver could just be snatched from the Classic ROM...
Just checking - you're talking about TTL serial here? / How about pads on the programming board for an optional level shifter / mount a 5V/3.3V level shifter if you're using 3.3V; or mount a RS232 transceiver if that's your need.
Yeah, sorry -- I meant 5V TTL, just the raw signal coming from the microcontroller's UART before being fed into any level shifters or whatever. I could definitely add pads for the level shifter and/or transceiver. I guess this is where I was looking at just doing USB because otherwise there are tons of various options that people might want and USB makes it nice and simple. But I can also see where diehard people might want to hook it up directly to a Mac serial port, or someone might already have a USB to serial adapter and don't want to pay out the nose for an FTDI chip added to the board. I'll see if I can give it options to work with RS232, USB, 5V TTL, or 3V TTL, with only the stuff populated for what each person wants, or something along those lines.
Here's where I chime in again about my ancient ROM Emulator Project!
Whew...I'm trying to follow it all, but basically you're saying use the upper unused ROM space as a way of reading from other media like an SD card or USB flash drive or whatever, by addressing a microcontroller connected to the SRAM chips on the special ROM SIMM, through an expansion board? (Presumably a PDS/NuBus card, otherwise it would take SCSI or serial or something to gain write access) And then once you've told the microcontroller what data to load, you access that loaded data (which is now in the SRAM chips) through the ROM space? My first thought is if you need the expansion board in place anyway, why not just leave the ROM alone and do it all through the expansion board? Just brainstorming...