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A decent sized city would have at least 1,000 abandoned buildings after that and you can reload the save to before you decided to be a terrible mayor and keep the observatory.
The extra amount of money should keep you afloat while your city is getting back on track. Watch for electricity though as most connecting houses wont be there anymore.
Also save the game before doing that. You can just reload the game and still have the observatory unlocked forever, if you don't want to bounce back yourself.
Turn off any mods you have that demolish or remove abandoned buildings and raise taxes or cut power or something to make your citizens move out.
They'll leave their buildings behind and each one counts as abandoned.
It should be possible to get that low health building and the one to have lots of dead citizens too if you 'accidentally' add pollution to the water supply.
Low water quality will make all citizens sick.
They'll eventually die.
Your hearses will be overloaded and the still living citizens will move out.
And now you should have 3 unlocked buildings.
Once buildings are unlocked, they're unlocked forever across all saves forever.
Just save the game before you try going for the award and reload it once you get it.
Alternatively go for it and then see if you can get your city to bounce back.