Why are you stuck on talking to him in order to pay each month? Of course you owe the late fees - you paid late. Paying your rent is never conditional upon talking to the landlord a little before rent is due. Not having an email should not be a problem You have a phone, don't you? And you know his number, right? Text back & forth. Also, who do you think you are sending him "work orders"? He probably ignored them because it is not your job to tell him what to do. Not your place to give him a work order. If you have a repair request, simply report that - as a request.
Certified Paralegal, with 25+ years' experience & with Landlord & Tenant law experience.