If I were to request a higher-tier droplet and deleted it because I don’t need it right now (but might need it next week or month), do I have to file a new request and wait again?

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Hello @itsTyrion ,

Once your account is set eligible for higher-tier Droplets, you are free to create and destroy resources as per your requirements. You need not have to file a Support request again.

On a side note, you can check out our Snapshot feature which lets you create a new Droplet with the content from the previous Droplet.
https://docs.digitalocean.com/products/images/snapshots/
https://docs.digitalocean.com/products/images/snapshots/how-to/

Hope this helps!

Cheers,
Lalitha