The roof is asphalt and looks like it has 8-10 yrs left on it. has some new windows and some old.

The road becomes newer asphalt before you reach the first duplex, so it was all developed together.

But if you have asphalt roofs or cedar siding, or boilers you have to plan for them.

However putting on an investors hat, I would remove and replace that, will cost about 5-8/sf to dispose, install new sheating, new asphalt shingle.

He's been responsive in the past so I'm confident he will be this time as well.Then today he emails saying that his father who owns an asphalt company is willing to seal my driveway for no cost just because.

@James HockerYou may be able to refinish the hardwood floor.If you have an oil stain on an asphalt drive, try mixing a past (1:2 or 1:3) of TSP and kitty litter with just enough water to give it a consistency like stiff oatmeal.  

like others said, fix up the fence, paint the deck (you can do it yourself); put crown molding up in the home; stainless steel appliances would've been nice and not that much more $. got some of that colored paint cement and paint the frontway/stoop. someone can reseal the asphalt driveway for $50-$100. tile the bathtub; change the closet knobs. have you called the agents who have walked thru for feedback?

A new 3 tab asphalt shingle roof cost roughly the same for a 1000sf home in Taft that rents for $600 or a 1000sf home near the coast that rents for $2400.I have some older homes and some years, maintenance and repairs can exceed my total gross income on a particular home.  

A tenant's vehicle leaked oil on the asphalt driveway of a rental property. 

The one CAM property manager I spoke with said the fee is for the maintenance staff to put out traffic cones for the moving truck parking, and to offset wear and tear on the asphalt from the truck.