Wire moving against the roof can damage the shingles and it's a great way for lightening to be conducted to a building, it should have insulated stand offs attached to the building to hold the wire away from a roof line.

If you don't want to, then tell them to do it if you are not worried about damage. 

I negotiated a $50 rebate, free headlight restoration and a high gloss wax job for the car...

@James Solis evictions don't report tenants that damage properties when they move out, or do other crazy things while paying rent.

Regardless definitely get all of the information and I recommend walking the place with a contractor you trust initially to get a feel for what kind of work it might need.It has some termite damage and generally a bit dated.

Recent water damage due to a busted pipe..they were on site the next day and I had a check for damages in just a few days. 

Love baking that into my lease that it will be paid for by tenant within 7 days of move out or will be deducted from their damage deposit for leases here forward.  

The home is a 1900sqft brick ranch 3/2 with a nice layout but it has been neglected long enough that there is definite water damage.

Unfortunately termite damage can extend into the in areas that are not readily accessible (covered by sheet rock, paneling and such).

. $500/month rent with no mortgage would mean about $150/mo for adequate insurance plus taxes.That leaves $350/mo to cover PM, which will be hard to find a good one in that kind of neighborhood, then there's vacancy cost, tenant damage, capex like roof and heater, plumbing repairs.It's good that you are looking for other ways to make a deal work, but I would pass on this one.