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Now, a 'sort of' cheaty way to do this... go to nexus and get the mod package installed. This has settings in the 'Credits' screen where you can alter the game play a bit. One of the things you can do is 'skip' daily objectives. Normally, you can only skip one per day. But, with that selected, you can skip as many as you want... thus skipping one's that don't give very good rewards and trying for lunch box rewards instead. That's still cheating but, not as much as using a method to grant yourself a ton of lunchboxes--such as using the save editor--FSSE.
Someone experimented with how many lunchboxes it would take before they managed to get 20 legendaries and it averaged out to take between 500 and 600+ before getting the total needed for the achievement. AND, I believe that was considering they'd already got the ones from quests to start with. So, yeah... a ton of lunchboxes. You could also just use FSSE and add them to your vault. Again, it's cheating but, it's a solo player game so, you only need impose whatever rules you set for yourself. It don't matter if you cheat really--aside from maybe the fact you don't buy any lunchboxes thus depriving the Devs of some profits, which is why they no longer support the PC version.
I just hit 18 of 20 legendary dwellers for the achievement with 302 hours played on the vault and 330 lunchboxes opened. All without cheating or low end farming.
Only '7 of 20' is seemingly incredible run of bad luck. I've always collected more of them with each new vault run I do... more than 7. Either RNG hates you or you didn't take the time to collect lunch boxes and / or wasteland discoveries--quests found in wasteland from explorers. It's worth noting, this achievement only counts the total for the current vault you are playing. It's not cumulative. For example, if you play a vault and collect say 3 legendary's but, then delete that vault and start a new one, those 3 previous ones do not count any longer. It must be 20 within the same vault. Basically, whenever you delete and start a new vault, the count starts over again at zero. But, steams achievement progress does not reset. It'll still remain at whatever the highest count last was... until you catch back up to that number again. At that point, the count will continue growing. Also, need to have Steam overlay enabled in order for achievements to update... I'm pretty sure anyway.
Wasteland quests do not reward any legendary dwellers directly, unless you mean you get them through the lunchboxes at wasteland quests.
Wasteland quests can reward lunchboxes, rare dwellers, legendary junk and legendary recipes. No legendary dwellers.
Legendary dwellers are from lunchboxes or overseer's quests. Lunchboxes can be obtained from both wasteland quests and overseer's quests.
See also:
https://fallout.fandom.com/wiki/Fallout_Shelter_random_encounters
https://fallout.fandom.com/wiki/Fallout_Shelter_characters#Legendary_dwellers
I think if it was a Steam mod / addon that I just need to click "subscribe", I'd do that.
But right now it involves looking into save edits or time adjustments. There's always the risk that the game might break from these things. There's been lots of reports about save corruption. So I'm not going through all that trouble or risk.
To me, I don't really need to rush those things. I'm fine with taking it slow. Don't care if I "finish" the game at all. I'd rather keep it clean and confirmed un-corrupted.
But if you want to do it, go ahead. I understand.