To view only what has sold on ebay go the category you are interested in then select the check mark on the left menu to view [Completed Listings]. That will give you a better feel for what is actually selling and for how much.
The only way to find out some of this stuff is to test it yourself. While I agree in not putting up thousands of listings, put up a few with your work and see what does happen. That may tell you more than anyone can here. Test, test, test.
Do people know to look at ebay for the type of $1500 Adirondack chairs you make? Probably not, and that becomes an issue if they don't know to look for it at ebay in the first place.
I'd start by viewing completed sales of wordworking products, then try to hone in on those things that are already working for others using ebay and selling woodwork.
You may need to redefine your business, change is sometimes necessary. For example butcherblock cutting boards might be something to look into where it is a small product, low price point and easy to ship.