I can help with The first part of your question. There are two types of daylilies: diploids and tetraploids. I can't remember the number of chromosomes diploid daylilies have (is it 22?), and many of the modern hybrids now have double the amount of chromosomes -- and they are not fertile with each other. So you have to cross dips with dips and tets with tets. However, some of the hybridizers now treat diploid daylilies to convert them to tetraploids -- very tricky and can be somewhat dangerous to the person handling the colchicine, from what I've heard -- and sometimes tet conversions revert back to dips... Many of the beautiful swaying spiders and UF's are diploids, but most of the incredible edges (pie crust, chicken fat, teeth and tendrils) are usually on the tets.
And as to the very end of your question, the introduction prices of daylilies will probably shock you, and I recommend you get into some of the hybridizers' websites to learn what they are. (That's why we love the Lily Auction so much!). Why don't you check out Water Mill Gardens and Floyd Cove Daylilies for starters...
Is all this confusing enough for you?