Given that he's got a long history in business but is struggling to cover $30k in Op-ex and marketing spend, my guess is that this is either not very well managed or is in distress.

One thing I'm struggling with however is my ability to really understand the local markets in some of the areas I've been targeting.Among a couple areas, I think Watsessing Ave in Bloomfield has great transit, appropriately priced properties (cash flow opportunities), and there seems to be some serious development happening (new supermarket and luxury apts just finishing a short walk east of the Watsessing Ave station).I've driven many of the streets and seen a few properties in the area to get a feel.  

They really struggle to pay the rent almost every month.

But I am struggle to see if I should down more or less (10% or 20%) on it.

Most people will struggle more with the maintenance and repairs but I was a contractor running a carpentry business at the time, so that was no big deal for me. 

I’m the oldest and I saw my mom struggle a little but she always made it work.

A lot of contractors struggle with cash flow, and he may have underbid the job.

If I'm struggling to fill a unit, then I may drop my prices or deposit, but that's MY choice and is not influenced by a particular applicant.

Quote from @Kyle Rader: Help me out We need more information than that to effectively identify your struggles and pain points.

Imagine if you scrutinized yourself instead of spending so much time trying to justify your struggles by placing the blame on others.