Declaring his candidacy for President now would be a really smart move for Trump. It would make his prosecution even less likely (prosecuting an ex-president already has a lot of resistance because of concerns about what kind of precedent that sets, but prosecuting a political opponent in the next presidential election makes those concerns even worse) and it would draw more attention to Trump, which is all he ever really wants.
The normal down sides for declaring early, it might hurt the GOP's candidates in the midterm by diverting attention away from them and energizing the anti-Trump democrats and fund raising limits under campaign finance laws, don't really apply to Trump. I don't think he cares about how other GOP candidates do (aside from the ones he has endorsed or put on his shit list), and he doesn't exactly follow campaign finance laws to the letter. (Why should he, given the enormous resistance to ever charging him with any crime no matter how brazenly he violates the law?)
I realize "Trump" and "smart move" don't exactly go together. But I think an early declaration of his candidacy would be a no-brainer for him.