If a tenant is constantly paying late and there seems to be a clear sign of struggle in finances, wouldn't I be doing a dis-service by offering the tenant to renew their lease and continue the vicious cycle?

Most states require 27+ days of continuous stay before they are considered a tenant and not a guest.

Long term goal is to continue building my portfolio of investment properties. 

End of rant - continue!

I’ll keep you updated as I continue my search but good luck!!

Hence, the search continues.

If that continues then I'm definitely out ( and we will see).

Let's stay connected and continue to learn from one another. 

We gave him an old lease that said he didn't have to pay water (we newly split the utilities in the unit) and he noticed we charged him for water and then we refunded him (although he continued to send us pics of his napkin math that says we didn't refund him enough).   

Here are thoughts on building strong vendor relationships:1.Timely Payments: Pay vendors promptly upon completion of work to maintain goodwill and encourage continued collaboration.2.Fair Pricing: Negotiate competitive rates without undercutting the value of their services.