They will likely just use their best judgement and not spend 100 hours researching the laws to make their decision. 1.

It's possible the first letter or summons will slap your tenant quickly into compliance, or you may go all the way to court/judgement/sheriff removal. 

Any creditors judgement will not.  

Dark stain can mitigate a lot of that, but it's really a judgement call on your part. 

I am not sure if the agent can look at the property and give me a proper judgement on whether to buy it or not.

You can pursue a judgement against the property owner for non performance under the loan agreement terms which would come up on a title report when they go to sell or refinance the property since a judgment search would be completed against the seller but that takes time and money.

Worst case you will need to seek a judgement if the situation can't be resolved otherwise. 

Seal it before the end of the 2nd for sure since that is when judgement becomes impaired. 

To attach the deficiency judgement to the primary residence, did you have to show some kind of conveyance or involvement of that property in the traceability of the funds, or was it just a blanket attachment to all assets?

Whether or not you have an LLC, if you are found to be grossly negligent, it could be you that is writing the check for the judgement, and depending on the state, it can be up to four times actual damage.