Q. Do I need to give him 1099? If so how? Do I need to get his SSN?
A. Simple answer: no.
It became a little fuzzy under the new 2018 tax law. Landlords are, generally, still not require to issue 1099 forms to service providers.
References: http://www.forbes.com/sites/irswatch/2013/03/06/should-landlords-be-filing-1099s-for-service-provide...
Q. If I pay him with cash, I can still claim this as my rental maintenance right?
A. Simple answer: yes. But, your burden of proof in case of an audit will be a little tougher. In addition to a receipt, it might be helpful if you bank statement showed a withdrawal for that amount in that time frame.
