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And yes, I did just buy the game.
Garages from the various safehouses often lose vehicles.
Vehicles you leave on the street often disappear.
When you're busted or wasted, your vehicle often doesn't get impounded.
So, always return your vehicle to a 4-slot garage.
Or use the protagonists' default vehicles.
You can always see where your personal vehicle is on the map, if it's destroyed you can get it back from your insurance. The police impound also works reliable.
Guess they just didn't bother to retroactively add it to single player.
AFAIR, there are mods that do so, if you bother and risk a ban when (accidentally) going online.
A semi-solution:
During story mode, you'll get the chance to do some assassinations for Lester, coupled with stock market manipulation.
Save them all (except for the first which is mandatory for progression) for after you've finished the final story mission, so you can maximize the winnings from the stock market.
If you've also done all side missions and extra money sources, you can get $1.5 billion per protagonist.
You're then so rich to simply buy a new vehicle whenever one is lost.