The Hermit reversed tells us that Emanuele may not have the qualities necessary to make an ideal financial decision. He may be too influenced by the opinions of others or not have enough experience in the field. It is also important to consider his motivations: does he want to act only for his own interest?
The Five of Wands tells us that Emanuele may be willing to settle and take responsibility for his financial decision. He could be a responsible and level-headed person, able to make well-considered decisions. However, the card also suggests that he may be too reluctant to put himself out there and risk more.
Bottom line, the cards don't indicate whether you should trust Emanuele with this financial decision. If you do, you'll need to keep in mind that it might not be the most ideal choice, but it's possible that he's willing to accept responsibility for his decision. The answer to your question depends on your assessment of the situation and your comfort with the idea of putting him in charge of your finances. So, the answer is No; while Emmanuel might be able to make a good financial decision, the cards don't provide enough information to tell if he would be the best choice.