I have a section 8 tenant who is just chronically bad with managing his life.

I have a chronically late paying tenant as well...pays around the 10th of every month.

Still, as a chronic fence sitter I envy you. 

Medical bills is one thing, and a landlord will be more amenable to help someone who has some chronic condition that left them broke.

So i thought i wold break the ice and tell you about me and because i would like to find people thatt are local to chat with or eventually set up a group meetup .Oh yeah i am doing this all with Chronic lyme disease, 2 young children and a very understanding spouce lol The method I used to choose which property was the 4 quadrant analysis.Income minus expenses equals cash flow and then figuring how much or a mortgage payment could be afforded to make sure there was still decent cash flow after the refinance of the BRRRR.

*Insert long winded personal story here*, and now I'm 49, chronically ill and exhausted, but finally in a position where, if I can figure it out, I think I could start some real estate investing.

The reason I pose the question is I constantly read and hear podcasts saying it's unacceptable to allow chronic late payments.    

After meeting with the three inherited tenants we soon realized that one seems to be a "professional tenant" (only has a verbal lease, pays $100 less than market rent, and works for a local property management company; which leads me to believe he knows his rights as a tenant and won't budge on anything unless it directly benefits him)The second tenant appears to be a chronic complainer, and the third tenant seems to be no problem at all.I received a call today from the second tenant notifying me that the "professional tenant" who lives below him, is smoking weed and cigarettes in his unit and the smell is travelling to the upper unit and has been affecting his health and quality of living.Apparently in Ontario, smoking in a unit is not grounds for eviction, even if it was stated in a signed lease agreement.

I'd focus on getting more applicants and not on trying to transform a chronic later-payer.

Many times people are in chronic foreclosure status, meaning they keep one step ahead of being foreclosed on, so you want to send letters repeatedly to the same people.