My Latin never was good enough to be begin with (and has since deteriorated) to judge the 'quality' of your translation, but I felt it read quite well.
One interesting challenge I could imagine would be non-Westron words, esp. names. Since you are equating Westron with Latin, you could also equate Germanic or Celtic hobbit names taken from legends and other sources with mythologically heavy names, such as from the Iliad. That could be linguistically thrilling. Obviously, it would feel strange to have names from the middle ages in a text in classic Latin (unless you take it again as a 'translation' from mediaeval Latin... the possibilities!).
Harder to translate might be the Old English, unless you're feeling bold and use 'latinized' Greek...
The difference in style, especially the courteous forms in Gondorian Westron vs. their lack in hobbit Westron could prove interesting as well. Vulgar Latin, as traditioned in the Cena Trimalchionis (Petron's Satyricon) springs to mind as one possibility to form a contrast.
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