Quarterly taxes and long term investment

Hi. I have a couple of questions:

1. I am a 1099er and pay quarterly taxes. Do I need to pay quarterly taxes on cryptocurrency sales sold in that quarter? 

2. How do I go about figuring out long-term vs short-term when my crypto has been moved from exchange to storage to exchange? Say, for example, I purchased 500 coins on August 15, 2024, and 500 on September 1, 2024...and then sold 500 coins on August 1, 2025, and 500 on August 20, 2025...can I count the 500 sold on August 20 as long-term holdings that were originally purchased August 15 or do I need to count it as coins orignially purchased September 1, since I'd sold 500 earlier?