I interpreted it more like "I have these 500 different cronjobs all spread out across $unit_of_time. If the system is down for longer than $unit_of_time and then comes back, does all 500 jobs start running instantly (since they missed their previous deadline)?"

Just to be clear, this isn't default systemd timer behaviour, you need to opt in by setting Persistent=true. If you have hundreds of jobs like this you need a proper queue and neither cronie nor systemd is the right tool because at that scale you'd surely need better observability