S-300 is still a very capable system today and 1990s' S-300 systems are only really a generation behind modern systems. They're about as recent as the systems on Ticonderogas and Arleigh Burkes that are very much still in service today.
S-300 (and S-400 which is really enhanced S-300) in their most modern configurations are incredibly lethal systems against 4th Gen aircraft that aren't accompanied by extensive SEAD/DEAD resources and jamming. But Ukraine has 1st generation S-300P, from the 80s. These might have been upgraded to S-300PT-1, giving them cold launch with the newer 5V55KD missiles.
6 hours from Russia and they still can’t take them out
If there's a level at which you don't have all three options, there exist political situations that can leave you vulnerable.
E.g. if the US has no proportionate response to a Russian tactical nuclear strike on Ukrainian soil, it may hazard towards not escalating.
Similarly, why the talking points of US response strikes for the past few decades have generally been 'this was a proportionate response.'
But after the last warning to the Houthis, I expect the next ASBM or large drone that hits a civilian ship prompts a large US/UK (and maybe France and Germany) strike.
The drones are relatively light, cheap, and can be launched with nothing but springs and wood. There's no value in the launch locations and in fact you can launch them from anywhere.
The RU missiles have killed plenty of civilians though.