I was attempting to force a little more skin in the game with a contractor that has done some work for me. 

I'm house hacking anyway so it doesn't make a huge difference I just wanted to attempt to use the VA benefits! 

@Deavin Cox It really is as simple as Wayne points out.Unfortunately, a lot of borrowers in your client's position don't want to face the fact that they cannot afford the home and become desperate in an attempt to save something that they really can't without doing further economic damage to themselves.Without knowing more details of your client's situation, I can give you only general advice.

I have ALL written communication from the tenant where they agreed to purchase and pay, along with the attempts to collect.

Some people aren't nearly as good as they think and their amateurish attempts actually causes them to lose money.If you think it's expensive to hire a professional, try hiring an amateur.That's not just a cute saying.

I must say that as a complete beginner, I'm a bit intimidated by attempting to navigate rental income, depreciation, etc by myself.

The inspection contingency Does allow you to cancel or attempt to renegotiate after you see the results...it does Not require the seller to fix or address any of the supposed problems you find during your inspection.

If they are on month-to-month or no written lease, you should absolutely attempt to purchase the property with that renter removed.

Also wondering if habitually late payments, no contact, no attempt to cure debt or provide a resolution, denial of entry for yearly inspection, proof of abuse of bankruptcy are all grounds to file a petition for immediate possession?

If there was a way to team them up and provide other kinds of assistance (access to counseling or some kind of shelter, etc), that would be even better - though it may be that they have already attempted such things.