Don't disparage things, just explain that it needs a new roof and partial rehab due to messy tenant.

Sometimes when you do owner financing, or other "creative" ways it can get messy!

I would agree with Lee that if your goal is to wholesale, REOs are a messy source of deals.

Living in a construction mess is a lot easier when you're younger.

The land next my rental has dead trees and is a threat  to my property, it is also generally a mess.  I

That can get messy if it happens.Oftentimes sketchy applicants "wave a fistful money" under the nose of landlord, hoping they will not do their due diligence and overlook something untoward in their background.I'm not saying this is the case here, but I would (a) not take the advance payment, and (b) I would vet this applicant at least as thoroughly as all the others.Lastly, in some jurisdictions (like the state of NY, for instance) it is actually prohibited for landlords to take any deposits/advances amounting to more than one month's rent.

I agree with Mike, this sounds pretty messy.

This can start to get messy if for example a WY LLC owns a NY based property.

I would not get into a subletting agreement with the current tenant as it can be messy depending on your local landlord/tenant laws.  

Well unfortunatly she is in the middle of a messy divorce, and can not afford the property on her own, and neither can he.