I'm not moralizing. You need to keep up with updates both for compatibility reasons and especially for security reasons.
Yes, I realize that there are always issues with upgrading. There is a good way and a bad way to upgrade. But it must be done, which is why backup and upgrade procedures are well-documented in the WP Codex.
As was pointed out to you here and here (and this is your third post with what is basically the same topic), there are major database compatibility issues involved in spanning such a large upgrade gap.
That said, you probably wouldn't have to upgrade through every version of WordPress. You could try installing WP 1.0 in a localhost environment and upgrading directly to 2.0 and from there to 3.0, or try 1.0 > 1.5 > 2.0 > 2.5 > 3.0. I believe that Apache is already installed on the Mac you are using, so it is just a matter of installing PHP and MySQL, or just installing a MAMP server. Once you figure out what works in a localhost environment, you could try it on a live server.
You probably are never going to see this feature, however. Partly because of the database compatibility issues, partly because most people upgrade on a fairly regular basis and thus wouldn't require it, and partly because of the tremendous amount of work (and we are talking in the range of hundreds of hours) to make something like this for only a handful of people.