I get a message saying (This apple tv is not eligable for this version) I believe it is no longer being signed. So do I go ahead and upgrade to the new software and wait for a fix or keep the 4.4.4 and wait for a fix.
What I have learned so far, Do Dump your 4.4.4 ATV2’s SHSH blobs with iFaith. You will need the signatures now that Apple does not sign but 5.0 4099 images.
With These signatures from your 4.4.4 device you can jailbreak your ATV2 by reading Jailbreaking ATV2 Running 5.0.1 or Less, After Apple Stopped Signing Older Firmware Versions - Seas0nPass - Firecore
Do not update to 5.0.4099 !