There are exceptions in which leniency can be granted but this most definitely is not one of them.

Leniencies of this sort can be done if the item is only a small portion of the trade, and/or if it is only slightly outdated: obviously you're not going to use 7 year old prices for example, and if its an 1:1 exchange and both hats are outdated, you wouldn't be able to properly determine which hat to use to update and which actually gets the update.

In light of that same argument, it makes no sense to take an outdated value for the bumble beenie here as it was priced less recent than the bucket; you would be using a 7 month old price to update a 5 month old priced hat (or 5 and 3 respectively at the time of suggesting I suppose), which is a definite no-go.

Another huge reason not to use outdated values is if the sale ends up well above (or below) everything else, as is the case here. both other sales are much lower.

So using the outdated value here is not going to work. Regardless of whether or not that would be allowed here, this update would not be possible since the buyer in this sale is also the one that resold it for 197, very strongly suggesting that the sale is an outlier as a whole.

As an aside, you're using a buyer that did not exist at the time of suggesting to justify excluding sales here, which also does not work. Buyers have been pushed up by bot overcutters and only one of them remains, in a market where clearly they are not going to have any success, so their meaningfulness is limited.

The only thing you can do is try to verify sale 3 which is very likely higher than 157 in reality, and then use that; otherwise, this will have to remain outdated.