Self-Study Classical Education

It's a great question with a broad spectrum of available answers. Before I recommend anything (even if you have unlimited money, you don't have unlimited time [:)]), I've got a few questions for you: Do you have an area you'd like to focus on (philosophy, theater, history, etc.)? Are you interested in learning the languages? Are you more interested in a particular era? Do the Greek works or the Latin works interest you more?

You could choose to focus on particular interests as Lew suggests. Another approach is to work your way through a best-of type of selection as in the Harvard Classics collection:

https://www.logos.com/product/33084/harvard-classics-collection

Answering those questions would be a good start for me, it seems. History is probably my main interest. Languages are challenging for me, so I'd want to consider the necessary time commitment carefully. And the ancient era is of higher interest.

If you don't have the free Perseus Classics Collection, it's great to have it. The problem for using this as an intro is that there's so much stuff it's hard to find a beginning point and it's hard to put it all into context. There's a little help in Noet's Greek Classics Research Library, but the focus there is on the Greek language.

If I were in your position, I'd consider the Bristol Classics Classical Literature Collection. This includes the slender volume by Timothy Duff, The Greek and Roman Historians, which looks like a good introduction to a topic you expressed special interest in. This collection also includes material on the poets and orators. It would be hard to understand any classic text without understanding a little of the larger literary milieu, including poetry, rhetoric, drama, and Homer. Many ancient writers constantly refer to these aspects even in their history writing or in their philosophy. And keep in mind you'll usually get a better picture of ancient historiography than you will of ancient history by reading ancient historians.

Regarding rhetoric that I mentioned above -- which was a discipline that occupied a major place in ancient Greco Roman education -- you may also consider the collection of essays edited by Stanley Porter, Handbook of Classical Rhetoric in the Hellenistic Period, 330 B.C–A.D. 400.

There are so many ways to go, but these resources might provide a good foundation. Others will no doubt have other good suggestions.

Given your name, you must of course read Virgil's Aeneid before anything else, if you haven't read it yet.