I was awarded close to $5k in tenant damages and back rent during the court hearing.

They ones that need new roofs, have broken pipes, no heat source, or have water damage.

That is way too much potential damage to let continue.  

She trapped us into signing the lease as 1) there were no reasonably priced properties to rent & 2) we were not planning on moving this fall, so no money saved, nor household packed.Her property needs new windows because they leak and we have had major water damage, bathroom vents to be installed & mold removal from said bathrooms.

Some of those building had extreme structural damage that would need to be identified by an engineer or architect. 

Obviously, lowering the fee and raising the rate is an option but that feels a little bit like spinning my wheels.At some point, if I'm dropping my rates far enough to compensate for a high cleaning fee, we get into the conversation of "is it even worth it to rent it at this rate and risk property damage, 4 star review, etc".

I'm guessing this is a shared house and she's renting a room in it.For her deposit, I'd only keep whatever expenses are related to clean up and damage.

Basically I want to know how much damage i did to myself for.....reasons. 

Anyway putting together a list of damage to file a claim if you have any advice please let me know. 

Also you need to figure out how you intend to cover inevitable property damage done by guests but there are plenty of solutions for that in the marketplace where guests pay a flat fee per reservation in lieu of a deposit and you get covered for an assortment of potential issues (bad checks, credit card chargebacks, fraud, personal property damage, etc.)