Any recommendations how I handle this situation?

Multiple books: The Book on Rental Property; The Book on Investment Property Investing; The Book on Investing in Real Estate with No (and Low) Money Down; Start with Strategy; Real Estate by the Numbers; and Finding and Funding Great Deals.

It will end up costing you unless you're already a skilled contractor type individual.Get to know your neighbors that maybe around your property, especially if you're in a HOA situation where there's a mix of STRs and residential properties.

Even if you find something to buy with $20,000 down, you should still have a reserve in place to protect you against unforeseen situations.

The best spot to find handypeople is not on those main lists, it's in local Facebook forums because you can find a question about handypeople and then see multiple people recommending the same person in the forum.

Let them know of the situation, get your insurance transferred and then let them go to work for you chasing down the deposit and what not.

We have noticed that no landlords comply with any of the student rental rules and regulations in Syracuse, NY but do not want to put ourselves in a situation in the future.

How have you guys grown from one deal at a time to multiple deals? 

It is in multiple states.

It depends on the projected performance of your investment, on your financing, and on your overall financial and tax situation.