How to negotiate the old, not the broken...

[Nick Dillaha]

HEY BP! 

Looking to buy my second home (owner occupied primary residence) and rent out my current townhouse and I need a couple negotiating tips to help me with my offer.

The asking price is $249k (150/sq ft), the owner has already stated that she's "easy going" and does not have a mortgage on the property that she paid $230k for back in 2008. The home was built in 1996 and needs $2700 in roof repairs (via recent inspection) because the house doesn't have roof vents and the skylights aren't up to code and are almost at the end of their life. She installed a new AC, granite counters, as well as a new lawn last year. There is tile throughout but the home needs some TLC... She put new granite on top of original cabinets and both bathrooms need new vanities, sinks, toilets, etc. Can i use the old cabinets and bathrooms as a negotiating tool? Can I still try to negotiate this even though it's not broken and just old? Also, I agreed not to use a realtor because she stated "I am more flexible if we don't have to pay realtors.'' Can I negotiate all 6% that she's not paying? Or is it reasonable to only negotiate what she would normally be paying my realtor?

I have two comps to go off of, two other homes recently sold at $157/sq ft and $131/sq ft. Both homes have pools (mine doesn't) and are 300-600sq ft larger. I was thinking about starting at $144/sq ft, then trying to negotiate everything else from this point down. This will be a buy and hold for us as a place to raise my future family. 

Please help!!