Thanks for the reply, I just now noticed I had actually had this same problem a year or more ago and posted it Error with wildcard on windows.
I also just noticed the reply, it seems from the reply back then that I would have to go through the namecheap API and program something myself? Or is there some way to get the dns-01 challenge to work already that I can use?
I'm still pretty confused how to actually get the wildcards working? Should I not be using the --webroot or the --standalone plugin and trying --manual? I'm going to try reading through more of the documentation from the reply I got last year tonight and hope that helps.