I attempted the achievement. I designed an engine with OHV before 1910. I let the research complete. I then bankrupted my company. (4-5 turns later.)

No achievement was triggered. Tried exiting and reloading game... nothing.

Played on Normal. Top 10 AI. NYC HQ. Only setting I changed was to increase starting skills by a bit. The warning at the bottom of the screen did not indicate that any achievements were disabled.

Is this a bug? Do I have to play on Hard? Did increasing the starting skills mess this up? Are 300 AI required like many of the other achievements? Do I have to actually sell the engine through outsourcing? Do I have to put it in a car?

I'm stumped.