Ok, I sat and compiled all the necessary screenshots to accurately represent the situation going on here.
What we need
1. A Director wants to send an ALL STAFF Communication.
2. We setup "Announcements" OOtB App on top level site where EVERYONE in company has READ access to the App except for the contributing Director and SharePoint Admins - they have elevated permissions.
3. We have some default and custom fields for the Announcement App: Title (single line text), Body (Multi-line text with enriched text enabled), Created (default), and a field named "Send Email" (Yes/No field).
4. Director accesses lists, and clicks new item.
4.1 Director inputs Title
4.2 Director inputs text into Body
4.3 Director decides if MS Flow should send an ALL STAFF email upon creation of list item by toggling "Send Email" field to "Yes" (default is "No").
5. IF Director toggles "Yes," then MS Flow to send an email to ALL STAFF.
The Problem: SOME users can see ALL images inserted into the Body of the item WHILE Viewing the email both in Outlook Desktop Application and Outlook Online, while OTHER users can only see the images when viewing the MS Flow email within Outlook Online, but NOT within the Outlook Desktop Application.
Below are four (4) Screenshots with a description immediately above each image...
Below is a snapshot of the list, in particular you are seeing the "Body" field in edit mode. As you can see here, this body contains an inserted image. The image was uploaded to /SiteAssets on the top-level of our Site Collection - which is a place all users have READ access.

Below is an image of the MS Flow we have created. I have some text within the image telling you what things are that I have hidden from view. The "Replace" function in the middle is a nifty workaround I found online, but cannot find the thread for it. Originally, in place of the "Replace" function we just had the Dynamic Value of "Body" but the images being inserted into the Body field for the list item were not populating for our un-affected users, so by using this "Replace" function we were able to get our known un-affected users capable of seeing the image.
The issue was... Flow was pulling a dynamic link from the SharePoint List meaning the url looked like this "/SiteAssets/image.png" versus it needing to be "https:COMPANY.sharepoint.com/SiteAssets/image.png." So we basically converted a dynamic link into a static (or direct link) via this "Replace" function.
Furthermore, as you may notice - in lieu of forcing the Director to insert their signature block every new announcement... We attempted to build the signature straight into the Flow using HTML (Yes HTML is enabled for the email in FLOW). The location of the .png file is in another central location in which all users have READ access to the image.
The line in which the creation of the signature begins is immediately to the right of the word "Body" on the left hand side... This line: <font face="calibri" color="black"><b>.....</b> which has text on the right hand side that states "Name of Person for this signature."
The line in which the signature ends is the line referencing "Company address in signature."

Below image is viewing the MS Flow email from an "Affected" user who is unable to see either image (the one from the item in the list, or the signature .png file stored on SharePoint) WHILE viewing the email in Outlook Desktop Application - but in Outlook Online, they see the images fine.

Below image is viewing the MS Flow email from an "Un-Affected" user who IS capable of seeing both images WHILE viewing the email both in Outlook Desktop Application and Outlook Online.

Part of me wants to thing this is an end-client Outlook Desktop Application disallowing a user from downloading received images, but we went over to the Trusted Center on an "Affected" users computer and allowed for image downloading from all sources temporarily, and that did not fix the issue.
Next we thought, well maybe it's a "Send Email" setting on the service account set up for MS Flow, but we couldn't find anything there.
We lastly compared Outlook Desktop Application settings between an "UN-Affected" user and an "Affected" user and couldn't find anything there.
Because we can get the images to render for some users and not others means this isn't an issue of being possible or not, but it yields only 1 of 3 possibilities... (1) Outlook settings on sending or receiving end that we have overlooked, (2) Issue with our Flow, although unlikely seeing as only select users are affected, or (3) an authentication and/or permissions related issue between Affected user and image location, although this is unlikely, because SharePoint permissions are right, not to mention, one of our "Affected" users is a SharePoint Administrator in O365 admin center with full admin capabilities over the Site Collection being used to store these images.
Any insight, even the smallest amount would be of most help to us.
Thank you.