Investors & landlords

"What is unbelievable is that there exists none such software! How about tradelog (https://www.tradelogsoftware.com/)? Can this help?"

 

Apparently that software does exist.  TradeLog says they can handle this situation perfectly; that seems to be their Raison d'être as they emphasize wash sales repeatedly throughout their site.  They offer a free trial so perhaps you can test it out and report back.

 

To a large extent the "nightmare" aspect of wash sales depends heavily on your volume and pattern of trading.  If you're day trading in more than one brokerage account and trading the same stocks across all the accounts then reconciling the activity can be difficult.  But if you're talking about a handful of trades across accounts you should be easily able to handle that.