Adding new roof, all new split unit HVAC to replace window units and paint/clean up the grounds.

If he has a clean record, make a separate agreement that he can stay there from (date) to (date).

I would suggest using local non-national banks they are eaisier to work with and you can establish a relationship just going to use them regularly instead of just poking in one day asking for what they have for you.

Is this easy to clean up and correct without taking too many things apart or will this require a lot of work?

Removing the previous tenants that hadn't paid rent or electric in years, new floors, new vanities, new toilets, cleaning the cabinets and shower to make them look new again and repairing all electric, windows, etc.

Removing the previous tenants that hadn't paid rent or electric in years, new floors, new vanities, new toilets, cleaning the cabinets and shower to make them look new again and repairing all electric, windows, etc.

Removing the previous tenants that hadn't paid rent or electric in years, new floors, new vanities, new toilets, cleaning the cabinets and shower to make them look new again and repairing all electric, windows, etc.

When you're working directly with regular people, all the terms are negotiable.  

The best idea would be to clean and re-point the bricks (if needed). 

Again, the bank sells loans, not houses.What ends up happening is that people regularly use the bank appraisal for the appraisal contingency in the sales contract.