When do you do that? If you mean changing the font extension in the msdash in order to load it from evox, xbmp, whatever... you either re-sign the modified msdash.xbe with the appropriate public key (oh yes you do) or you have invoked PBL to load a hacked bios which disables the signature check.
To your other suggestion about making the exploit either set a default time or check a flag to see whether the time need setting or not. This is kind of what the reloaded and bigfonts do (please correct me if I am wrong!). Or at least are trying to do. The catch here is that there is a "time-issue" here, or a race going on if you like. In order to have real control of the xbox the actual exploit code of the hacked fonts needs to be reached before the bios finds that the clock is not set. It is my understanding that the loop occurs if the exploit code of ernie (any version) is not reached (and executed). Why is it not reached. Check out :
http://forums.xbox-scene.com/index.php?showtopic=95297&st=0 Ernie has a big exception net that is supposed to catch an exception generated by the hached fonts (by its alteration of the memory). After this exception is caught multiple jumps are made to reach the exploit code. If we dont get here in time the clock-setting code in the msdash could be called - it needs the (real) fonts to work - it tries to load the hacked ones -> loop
I guess it is a bit at random which thread generates an exception and is caught by ernies exception net so after a number of loop we could be lucky that we hit the net in such a place that the exploit code is reached in time so that that what ever clock-rescue code is included (reloaded,bigfonts,mechfonts) can do its magic. Maybe this is also the reason why some people have success in escaping the loop by stalling the xbox in various ways (network cable, statched audio cd etc.). If no such code is included (original free-X fonts) the xbox will loop forever.
Anyway. This is just my picture of what could be going on. Someone with more insight is welcome to correct me... But the bottom line is that before coming up with ways to check or set the clock via the exploit we need to find a way to increase the propability of actually reaching the exploit code of Ernie.