Be sure to research the advice you are getting before taking action. In this unique and ever changing environment the regular rules do not apply.
1. Do you have a loan on the property and if so is it federally backed? If you do not know call your serviced - the company you pay your mortgage to - and ask them.
2. If you do NOT have a federally backed loan you need to focus on your city and state regulations about evictions. New York is not Owner friendly so my guess is you will be under various restrictions which may increase the notice required or prevent evictions. If you can evict do it immediately. Go to the local court website and follow their rules to the letter. You may have to prove you do not have a federally backed loan.
If you DO have a federally backed loan you CAN NOT give notice until July 26th under the CARES Act (moratorium on asking tenants to leave ends at midnight on July 25th I think. On 26th you must give a 30 day notice no matter what you lease says.
Unfortunately, it is likely the Moratorium will be extended this week in the new relief bill. My guess is it will be 120 days but might be to the end of the year or even into next year. We will know by the end of this month. You still must consider local and state regulations in addition to cares act restrictions.
Under the CARES Act you cannot report him to a credit agency for rent not paid during COVID-19. You also cannot charge late fees. Don’t take a chance of a judge making an example of you.
3. If you are struggling to pay the mortgage look into forbearance. Call your servicer for information and read every word of the agreement before signing. Be careful of offers to “modify” your loan, this could affect you negatively on future loans. Ask what the consequences will be in future lending decisions.
4. Talk to your resident about:
Unemployment- have they filed? Almost everyone, even independent contractors are eligible. If it has been hard or frustrating so he has not done it encourage him to try again. Claims are going down so easier to get through. Benefits are retroactive. Also they are likely to be extended by Congress.
Car payments can be deferred and sometimes partially forgiven. He should contact the number in his monthly statement and check.
Utilities can be deferred or forgiven he should call each utility including phone and cable.
Student loans - if he has any he should stop automatic payments because no payments are due until the state of emergency is lifted. He does not have to do anything to get this benefit it is automatic.
Local rental assistance programs - look to see if there are any and help him apply. Be careful that accepting these funds does not commit you to longer eviction moratoriums. Some programs come with strings.
If there are job services or listings available in the area provide those too.
Finally, you mentioned his girlfriend. Is she living there too? If so is she on the lease? If not I would ask to put her on the lease and run a background and credit check and follow your typical process to get her on the lease.
Sorry for the long post, hope it helps!