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?

Hence, the search continues.

I would recommend finding a way to continue to practice in some capacity, at the very least to cover living expenses.

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

If these servicing companies can’t get their act together and this pain in the neck activity continues, we may just pay these loans off entirely or refinance with our local credit union.  

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).   

I’m still young and plan on continuing to put all my money in real estate for the next 10-15 years.

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

It’s more like having a continuous, flexible funding option rather than a one-time transaction.It doesn’t require much effort compared to getting a loan traditionally:When you "get a loan," you typically have to go through banks or rely on friends and family.

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