So, in the event anyone comes across this same issue and is without a legitimate workaround, I "came up" with one the other day when I came back to solving this issue.
The first postback issue seems to stem from the clearing and repopulation of a container control (placeholder, panel, updatepanel, etc.). As I had the user click on a menu item that would then clear and load usercontrols into the container, the usercontrol being referenced on postback differed from the new one being loaded. Bear with me on how I will attempt to describe the situation...
The last loaded usercontrol is referenced on the initial menu click, before the menu click event fires and then, the container is cleared and the new usercontrol is loaded from the menu click event. This does not happen when there are no controls loaded in the container (initial startup). As the usercontrols are added dynamically, I have a method that reloads the currently loaded usercontrol, it is placed in Page_Init. This event, along with PreInit, _Load, all fire before control events, and was the cause of my problem. The fix is, as will be obvious with more experience, is to add an if statement to both the usercontrol load method and Page_Init (or wherever you have the load method) that determines what is causing the postback. As, I only want the user to click on menu items to move within the numerous tasks, I just made sure that if the menu item click is causing the postback, then, do not run the load method in Init, but, anything else that causes postback (for me, only within the user control), the load method within Init will only fire then.
Additionally, the if statement is necessary within the load method, to make sure all of controls within the newly added usercontrols contain default/empty values, essentially whatever defaults you want the user to see when the control is first displayed, in my case I had:
if (Page.Request.Params["_EVENTTARGET"].Contains("Menu1") == true)
{
uc.Clear(null, null);
uc.SetBoundControls();
}
)
Hopefully this helps someone else, or sparks a thought towards a better solution.