Dear DEHYDRATESINC
I am an independent advisor, and I am trying to help other users in Community with my experience in Microsoft products.
If you want to have the image in signature and to be able to resize it, you need to have Office 365 to unblock this feature or use a workaround.
In order to get an image to the signature it is enough to copy/paste the image to the signature box https://outlook.live.com/mail/options/mail/mess... I just have checked this and changed my image and it works. More about signatures you will find here https://support.office.com/en-us/article/create...
If you cannot paste it, then it might be a browser issue. Try to use another browser, and In Private mode. Sometimes extensions or cookies can block authorization. It is also recommended to clear cache and cookies from time to time. In this article you will find the way how to delete the cache and cookies for most of the browsers https://www.wikihow.com/Delete-Tracking-Cookies
As I understand you are referring to new UI of Outlook. I would also suggest to use this help to get familiar with all the features https://support.office.com/en-us/article/get-he...
Note: This is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.
Please share the results!