1st- welcome to TeaChat!
2nd- as for there being thousands of dollars of tea you want to try, join the club!
I'd just experiment with the more popular teas until you find the category you're interested in focusing on and narrowing it down from there. But think of it this way, endless amounts of new teas mean endless discovering of new joys
3rd- *some* teaware (pots/cups) can inhance the taste of the tea, but oftentimes you will find that it can be tea-specific, i.e.: yixing teapots aren't good for green teas but oolongs and pu-erhs can be quite tasty if you pair them with the right yixing. ALSO, some people have certain features (be it aesthetic, texture, etc) that personally inhance the tea drinking experience, I love the feel of glazed porcelain on my lips while I breath in the scent of a great tea for example!
Hope this helps