This is what I use on my PC at home which is not windows 10. But this is streamlined and somehow always logged in. This format as you can see on the right side of the screen has all my options easily accessible and never times out, ever. It seamlessly allows me to fill and sign with my signature which it saves, and get others to sign easily as well. The other platform above makes me literally save the pdf as a signed copy. Then upload the signed copy into "sign" and get others to sign if I do it manually. If I try doing the seamless path using the tool bar on the right from the picture above that timed out, each time after I fill & sign, and move to "get others to sign" it uploads the document and then times out?!

Hi Aaron,
Sorry for the delay in response.
The first screenshot you have shared shows that you have opened the PDF in an older version of Adobe Acrobat.
It seems to be the Adobe Acrobat XI version. It is an old and unsupported version of Acrobat.
In the second screenshot, you are opening the PDF in Adobe Acrobat Reader DC.
It is a free service, where you can Fill & Sign the document.
As you have the Adobe Sign subscription, it redirects you to the Adobe sign page as you are signed in with the same Adobe ID under which you have purchased the subscription.
I see that you have the Adobe Sign subscription.
If you need to send the document to others for signature, you can directly sign-in to your Adobe Sign account for this.
Please use this link Sign In — e-signature and e-sign Software Solution — Adobe Sign to sign-in to your Adobe Sign account.
You may also install the Adobe Acrobat Reader DC on your laptop from here Adobe - Adobe Acrobat Reader DC Distribution
Once the application is installed, sign-in with the same Adobe ID and you will be able to send the documents from there as well.
However, it is suggested to use the Adobe Sign account for signing and sending documents for signature.
You may refer this help document Adobe Sign Help | Adobe Sign Help.
Let us know if you have any question or need any help.
Regards,
Meenakshi