If they're worried about your experience or it's not a great fit, then consider the standard approach: live below your means, put away something each month for investment, be ready to deploy when you've achieved the target.Now realizing this is getting long, but it's helping me fight my insomnia.

I had one chronic one before that who's job had the salary cut about 40% due to the oil field slowdown. 

My DTI is too high (child support will be a chronic hurdle) .I'm looking at bringing in other friends to be names on the loan.

their chronic tardiness along with the unknown number of occupants along with your concerns of drug use is a recipe for disaster.  

If the property needs to be renovated to be rent ready do not cut corners on the renovations, you do not want to deal with chronic maintenance issues in the long run.Make sure you screen the tenants, the better quality tenant = longer lease term / less turnover, pays on time, and normally will take better care of property.You want to find a transparent and reputable property manager with boots on the ground = this can be a huge factor in having a successful real estate investment.

The credit history will allow you to see if a lower score is the result of a single traumatic event (divorce, job loss, etc) or a chronic pattern of not being able to manage finances.

If you can't shut them down, you need to get rid of them.Every Landlord can avoid chronic complainers by:honestly disclosing the condition of the home prior to application/leasing/occupancy;including a disclaimer in your lease that says the applicant was given a chance to inspect the home and they are accepting it "as is, where is" unless cleaning/repairs/improvements have been agreed to in writingIf they insist on complaining, simply respond back by pointing them to the disclaimer.

This sounds like the kind of choice made by the chronically middle class.

The city has tagged both units as uninhabitable, but allows entry to retrieve belongings (it has heavy damage but is not in danger of falling down).To add to the saga, their credit is far worse than it was when we placed them in our unit due to the husband having chronic back issues that have prevented him from doing his job full time. 

But based on your account, you were not chronically late.