Pending roof replacement - risks during winter season?

[Sylvia Schumacher]

Hi!

I am looking into a short sale in the Cleveland area. Unfortunately, the roof looks pretty scary and as it's a short sale, I don't expect to be able to repair the roof myself before winter arises. 

Would anybody know about the risks this kind of roof brings? Do you think it's a red flag and I shouldn't even put in an offer in the first place?

I'd appreciate any thoughts!

Thanks!