Hello Corey,
Ah, the joys of landlordhood. While trying to navigate the eviction process is exacerbated by the COVID-19 issues, I feel like you have given this tenant more than enough leniency. Some people just don't realize that they could get much more leniency if they reached out to the landlord and discussed their situation. There are people who refuse to believe that some landlords are actually willing to help.
Whatever the reason may be for his silence, I think it might be wise to consider upping the stakes. This tenant might well be aware of his rights and the position the city and the state have adopted during these times, but just because they are putting a pause on evictions doesn't mean that rent isn't still due. And as the word implies, a "pause" is just that. Even though he doesn't appear to be responding to you, you might want to write up a letter letting him know that rent is still due, that you have given him chances to work with you, and that if he continues to ignore you and fail to pay rent you will be taking his situation to court when they reopen. It might be a good idea to let this tenant know that an eviction on his record will severely limit his ability to find a respectable rental down the road and that if he has unpaid rent, it will impact his credit score once it's sent to collections. You can remind him that most apartments call past landlords to check for references.
Also, make sure you keep thorough documentation of all of your correspondence with the tenant. If you do take it to court and you can prove that you've actually reached out to him, that will be to your benefit. Many a tenant have played the dumb card: "I didn't receive any calls or nothing."
Giving him a 5 day notice might be as futile as trying to get the court to process an eviction right now. And once you give that notice, from my understanding you can no longer collect rent payments. I personally would give him a letter outlining what I mentioned above along with your notice that you will not be extending his lease. If you want to give him another chance, send him the letter and also add in that if you don't hear back from him with a day or two, you will be sending him your notice of not extending his lease.
And I am sure someone will tell us why this isn't a great idea, but you might even consider trying to find another accommodation for him. See if you can't find another comparable apartment in the area and tell the tenant that if he cleans up the apartment to your satisfaction, you'll refund his security deposit in full so he can use that to move into another place.
Despite that a problem tenant generally causes you more problems and headaches, I always feel like its a reasonable thing to give them the two options: clean the unit up to the point where I don't have to do anything to rent it out again, get your money back, and move on with your life; or deal with the eviction process, the collections process, and then having the eviction on your record. Even if the tenant for some reason prevails in the eviction process, the fact that an eviction has been filed against him will still be public record. This method, commonly referred to as "cash-for-keys," is just as beneficial to the landlord as it is for the tenant. You don't have to pay for the eviction process. If the tenant agrees, cleans up the unit, and moves out in the allotted time frame, then you can get another tenant in rather than spending a month or two without receiving rent, then having the tenant leave your unit as messy as can be.
I wish you the best of luck in working with this tenant. If you have any other questions or concerns, please feel free to reach out.