I’ve been rebuilding the meagre Latin I picked up in college in the 80s and I’ve found late Latin to be a bit helpful for building confidence—Beeson’s Primer of Medieval Latin and the Vulgate Bible have been my primary texts of late. With the Vulgate, I’ve been painstakingly translating by hand every verse (I’m not as diligent as I should be so I’m only up to Genesis 17 despite a few years of doing this in fits and starts). With Beeson, I reached the point where by the time I got to the poetry section, I was relying much less on wiktionary (which is handy because you can find most words by their inflected forms rather than having to know the correct dictionary form). I doubt I’ll ever be fully fluent, but I’ve got a pretty solid reading knowledge these days.