It is going to get expensive so i would advise your client to ‘get creative’ as suggested already and/or perhaps offer them a monetary ‘incentive’ to leave and then hire someone to secure the property which may even mean boarding it up.  

Rabbitt hole #2: Then went down another rabbit hole of taking my cash and investing into another smaller condo outside of the area into other towns, but I think my DTI is too high due to my self employment.  

I have seen writing on the walls, spilled paint or juice stains in the carpet, holes all over the wall.

He is still trying to climb out of that hole.

And while to them, their stuff may be most of what they own, in terms of monetary value you're at much more risk with your real estate than they are for their miscellaneous stuff.

That being said I’ve come up with an idea that I want someone to pick apart the holes in the plan and possibly answer some of my concerns. 

Then, just follow the breadcrumbs.The biggest barrier to REI success, and just starting, is the lack of a complete REI plan, based on exact monetary goals (numbers with $$$$ in front, not %%% behind).

Question: where’s the best place to find those smelly crap holes outside of an auction?  

I told her that as long as there are no holes drilled in the outside of the house or electrical that needed changed and that they were aware that any damage to the windows or doors would come out of their deposit…I have no objections to cameras. 

A deadbeat tenant won't normally care about their (lack of) credit, however by certifying and recording the monetary judgment you receive after court, you MAY see some return of those lost dollars if or when that tenant needs to clear a judgment off their record.d.