Great thread!
I was a late comer to computers. First was an Amstrad 286 with a 20Mb hard drive. I put every piece of software I owned on it and wondered how I would ever fill up the rest. Eventually I used disk compression or whatever it was called then, so that my 20Mb HDD was compressed to about 35Mb of which 10Mb was used with the software!
Then I took the giant leap to a 486 DX2-66 with a 420Mb HDD. Not only that but instead of the standard 4Mb of RAM I paid to increase it to 8Mb. How much? I still have the original receipt; $300 for the extra 4Mb. I'm saving that one for my grandkids!