Ultimately, that’s up to you. Gray skies can be alleviated by “sky replacement” for up to two front elevation photos. Rain does not show up in photos except as wetness on the ground (unless it’s raining very hard). Video is more affected by those two problems.
Snow cover is problematic, but if a listing needs to get on the market, there’s little we can do at the time. Often, when the weather is better, we are asked to set up another appointment for fresh, unclouded exterior photos.