Having booked my tickets online well in advance for Monticello and making sure I had ample time in Charlottesville (both preferrable), I felt this might be an interesting first stop as we made our way South. Charlottesville, which is dominated by Jefferson's legacy is in the midst of an ongoing re-examination of the man and Historical truths long ignored (particularly for visitors pre-1999 to Monticello). Ta-Nehisi Coates (author: Between the World and Me, The Water Dancer, etc), after visiting Monticello said, “They will tell you the truth. There is a broad and growing movement to tell the truth.” When visiting Monticello, you will experience tours that highlight Jefferson the Slaver, Writer, Architect, and President. The Hemings family will be featured prominently, including both John Hemings and Sally Hemings (mother of at least six of Jefferson's children). From 1993 to 2001 was the initial period where the interpretation of Monticello began to change to tell a more complete History of Jefferson and the people who lived there. 

The Second Introspection began in 2017:

After the "Unite the Right" rally in Charlottesville in August 2017, the city has experienced a racial reckoning even more acute than most American communities during the past few years. In fact, the week before we arrived, the Robert E. Lee Statue was finally removed nearly four years after the infamous rally that sought to protect it. Afterwards, the city council renamed the park and other Confederate Monuments were taken down. The Robert E. Lee statue was commissioned in 1917 and erected in 1924, which corresponds to both the monumental film "Birth of a Nation" which spread the "Lost Cause" myth and the emergence of the 2nd Ku Klux Klan. The vast majority of these Confederate Monuments and Memorials were commissioned and built between 1896 (Plessy v. Ferguson, which codified racial segregation) and 1921 (Tulsa Race Massacre). The Lee statue stood for nearly a century.

What does this have to do with the inscription of Monticello and the University of Virginia in Charlottesville in 1987?

Criterion (i): Both Monticello and the University of Virginia reflect Jefferson’s wide reading of classical and later works on architecture and design and also his careful study of the architecture of late 18th-century Europe. As such they illustrate his wide diversity of interests.

Criterion (iv): With these buildings Thomas Jefferson made a significant contribution to Neoclassicism, the 18th-century movement that adapted the forms and details of classical architecture to contemporary buildings.

Criterion (vi): Monticello and the key buildings of the University of Virginia are directly and materially associated with the ideas and ideals of Thomas Jefferson. Both the University buildings and Monticello were directly inspired by principles derived from his deep knowledge of classical architecture and philosophy. 

Based on these criteria, very little. Yet, how can you visit these historic sites and not engage with the full History? For more information about the History of the enslaved people at Monticello, browse this page from the official website "Slavery at Monticello".

In regards to Jefferson the Architect, perhaps the most impactful example is the Academical Village at the University of Virginia (Charlottesville). Criteria iv specifically, seems fully met with Jefferson's Academical Village and the landscape today remains impressive even 200 years after its founding. I do not believe criteria i or criteria vi are met in either property, but then again I am not an expert.