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Moral of the story: if you're going to backdate documents, use a VM with period OS/software. It probably wouldn't hurt to use antique printers as well.
Use old paper and old ink, too.

It's probably possible to tell that ink was applied to paper recently, even if the ink and paper are both old, but I'd expect that the longer it has been the more uncertainty there is so you should be able to fake an N year old document without having to let the ink dry or set or diffuse or whatever it does for N years. I'd assume that there are ways to speed this processes up, too.

I have no idea what the curve looks like though. This may only be practical if you aren't in a hurry. So, faking a document that you've just found out you need and you need soon might not be feasible, but faking something like a mint condition vintage comic book might be possible.

Probably should also use vintage staples or glue or whatever was used for binding at the time you want to claim the document is from.

This is really the kind of thing you want to plan ahead for, rather than find yourself on eBay trying to find a specific make or model 50 year old printer that works.

Any competently run evil organization that has a decent budget (Hydra, KAOS, Cobra, AIM, etc) will regularly buy copies of the document production equipment and supplies used by contemporary businesses, governments, and hero groups and keep that equipment working and well maintained for several decades for retroactive document production.

>It's probably possible to tell that ink was applied to paper recently,

Confidence on this measurement is probably very low. Documents in a basement in Miami (they don't do basements in Florida for a reason) will age very differently to documents in an attic in Tuscon which will age very differently than documents in a garage in Fairbanks.

Better use an old printer indeed, since modern printers can have tracking dots with a timestamp and a serial number of the printer, which both can give away the backdating (https://en.wikipedia.org/wiki/Machine_Identification_Code)
Moral of the story, don't cheat. That being said it seems to me there is a business model here, sort of a document analysis service to pick up on these subtle indications of document properties. If I was trying to dispute a falsified document in court this sort of analysis would be quite valuable. I would love to see a Web service that allows customers to upload a particular document for verification.
Don't forget the paper and ink. The best would be to simply write this by hand.
Seems like someone could create a little program that could let you choose time specific fonts. Though I really can't see much use in such a program other then something someone might produce just for practice.
Any situation where you need era-appropriate typography and are serious about it even when you’re not trying to be deceitful. Eg. movies, games, and their various marketing material. Though usually if you are serious you have money to hire a graphic designer.
Or just hire a nerd with all-sixties IBM gear :)

https://www.youtube.com/watch?v=VMDP3Iz6D6A

(although the pedantic in me notes that he used the wrong selectric ball (prestige elite vs large elite) for the license)

Let's go the other way too. Are there any websites that accept an image and via image analysis able to tell you things about the doc?

I wonder how much you could infer about a doc given its margins, font, kerning, leading, etc. "This looks like default settings in Word XP"

Anyone smart enough to use such program would probably be smart enough to just google the correct fonts.
Tangential to the main point of the story, but why were this CEO’s homes up for grabs when his company collapsed? Isn’t liability limited to the company?
He was sued as a director of the company for breach of fiduciary duty (in part with respect to executive compensation).
"Piercing the corporate veil"
lol. wouldn't surprise me one bit if there's an additional watermark buried in tiny variations in the kerning or something as well...