I had no issue with the toolchain, as I happened to work on a game (ZZT) whose toolchain of choice was documented by the author himself (well, he was off by one

I had no issue with the toolchain, as I happened to work on a game (ZZT) whose toolchain of choice was documented by the author himself (well, he was off by one Turbo Pascal release). Lucky! What took me the most time was actually the beginning: building a mental model of what assembly patterns map into which Pascal patterns, and finding good areas to start writing code from. In hindsight, I should have probably started by generating inline assembly equivalents of each procedure/function. The ending was relatively smooth sailing in comparison, but it is of course much easier if the compiler you're targeting doesn't do much in the way of optimization passes, so it's not representative of decompilation work for more modern targets.