you accept the small risk of the listing ending during a server down/bugged situation
Most managers would probably accept a small risk, but the problem is these crashes have become so commonplace that the risk is quite significant now. I've played this game for quite a while and prior to the past two seasons, I can't remember things like this ever happening.
I know you guys are moving to a new server soon, which should improve the stability issues, but in the meantime maybe introduce some contingency measures that delay transfers in case of the site crashing.