Hello and thank you for the opportunity to assist you. My name is ***** ***** I will do my very best to answer your legal questions.
Unfortunately, the provision that he will owe you $50 per day would not be enforceable regardless. Penalties are not enforceable in contract law. Landlords can get away with liquidated damages (i.e., damages agreed to in advance), such as a late fee, but such damages must be reasonably related to actual damages. In other words, $50 per day would not be enforceable unless you could demonstrate to a judge that you actually suffered $50 per day in losses as a result of the breach. That is unlikely to happen.
The other issue, of course, is what you've already pointed out ... that the tenant didn't even sign a lease for the second year. So, the bot***** *****ne is that you would not be able to enforce the $50 per day fee. Still, you can evict him and sue for actual damages (i.e., unpaid rent, physical damage to property, if any).
Does that answer your question? Please let me know if you need clarification, as I am happy to continue helping you until you are satisfied.