I remember those days of Bitcoin being less than $1 each. My first experience with Bitcoin was a customer for my PR company. He needed some work done, asked if I had ever heard of Bitcoin, I said I had but did not have any way to get in. We agreed on the price for what he needed done, $50 in Bitcoin at a time when that was something like 1.05 BTC.
He helped me setup a wallet and such, sent the BTC over upon receiving the work (a press release and a cold contact email - I was cheap back then).
I then went on to forget about Bitcoin till I heard about it on the radio. It had hit $1,275 and radio stations were talking about it. I then went home, found that old computer (almost threw it out when I upgraded), waited for nearly 3 minutes as Windows XP fired up (old hardware would be a complement to what I was running there).
Had I held onto that BTC that would have definitely been my most valuable work to date. Lol.
The 10,000 BTC for pizza was done at a time when Bitcoin really had no value. Back at that time it was literally like Doge value levels. A few hundred or so to a buck - hence the 10,000 needed for what was about $20 worth of pizza.
The deal was brokered by a gentleman in the UK I believe who accepted the BTC in exchange for the pizza. He made an international phone call to a local pizza place, ordered the pizza and gave them the address. The pizza place took it as a normal order like any other they would take that night.
Someone made out like a bandit on some pizza and an international phone call.
Have you read up on that one guy that threw away an old computer that had something like 20,000 BTC on it? I will see if I can find the news report, he was arrested at least once for trespassing in the dump trying to find it. I cannot say I blame him for at least trying.
Edit to actually answer your last part there.
The way PayPal is going to do it is quite similar to Coinbase and Circle back in the day. You won't have to sell crypto to buy something in fiat. It will happen automatically so you only sell what you need and only what you need.
RE: PayPal Soft Launches Crypto Currency Options