E-sign templates

I'm using the same program to try and do something similar. I am trying to make it so every time I send out for e-signatures, I don't have to manually change the date boxes to autopopulate when the signature box is signed. At first my search took me to this https://helpx.adobe.com/document-cloud/help/create-template.html but it gets worse.... I go through the online browser app instead of the desktop, make my template, then save it. Go to the ONLINE browser version of acrobat to find that template I just made. It does NOT show up in any Desktop adobe software (I manually synced to try and circumvent that issue) meaning, in Acrobat desktop's cloud files, desktop cc suite's cloud files; it is nowhere to be found. So I went back to the online app of acrobat, download the template to my computer. Upload that file to my desktop cloud and desktop acrobat. Cool, now I have the template that I don't have to edit every time I send it out. Click File>Request E-Signatures.... and it pulls up the same prompt as before, but without a file. Click select file, select the template I am currently using. Sends Could Not Send Unsupported file: "Se Contract.pdf" select another file and try again. So clicked cancel, try again, and it freezes.

At this point, I think the only way to use the template is online. Which I haven't used, it's a lot slower than the desktop version for me, and its layout and UI is different enough for me that I really would prefer to avoid it.