I think a potentially better way would be to segment the market up to today but take half or 10% of all the stocks and make only those available to the LLM. Then run the test on the rest. This accounts for rules and external forces changing how markets operate over time. And you can do this over and over picking a different 10% market slice for training data each time.
But then your problem is that if you exclude let’s say Intel from your training data and AMD from your testing data then there ups and downs don’t really make sense since they are direct competitors. If you separate by market segment then does training the model on software tech companies might not actually tell you accurately how it would do for commodities or currency training. Or maybe I am wrong and trading is trading no matter what you are trading.