Chewy, welcome to the BE site. You sound a bit like a child in a candy shop. You seem to be quite taken with bourbon/tennessee whiskey but have a limited but expensive selection from which to choose. I think the questions you as are good ones, but ones that none of us can really answer in a way that would offer you any real satisfaction. The questions you ask must be answered for you by YOU. Personally, I think the Dickel whiskies are very good and better than all Jack Daniel's whiskies except the JD Single Barrel.......... and they are usually a bit cheaper.
In my opinion, you are trying to make definitive judgements about American Whiskey way too early. Your palate will change as you try more whiskies and even the same whiskies will taste a bit different at different times. Since your selection is limited and not cheap, try different whiskies as you can find and afford them........ but do not make very many decisions as to which is the best just yet. Instead of looking for the best that is available to you, look to enjoy as many as you can to find out more about your own palate....... and give yourself time, no need to rush this, because, at its best, whiskey drinking (in proper moderation and with proper respect) is a lifetime, everchanging proposition. What you enjoy this year (bourbon, rye, scotch, irish whiskey, cognac, or whatever) may not be what you prefer next year........ and so much the better say I.
Do not go gentle into that good night,
Old age should burn and rage at close of day;
Rage, rage against the dying of the light. - Dylan Thomas