Seems like you are pounding the pavement to get listings?

I'd rather of a metal or commerical shingle roof instead of an asphalt shingle roof.

The work I will need to contract out include re-finishing the hardwood floors and I would like to level the (already semi-flat) back yard and pave it with asphalt as there is currently no off-street parking but this will yield 3-4 spots. 

AND hard surfaced if possible(concrete,asphalt,fly ash, plastic)

You just need to find a realtor who is willing to pound pavement for you.

Made small improvements like paint, added a huge deck for the apartment over the garage and fixed the small issues that the city had with the property, like removing a strip of pavement that was 1' too wide.  

Get quotes on some replacements for the ones that are in the worst shape.I'd personally tackle landscaping AFTER the pavement/parking issue.I highly suggest you make an Angie's List account so you can find local contractors (with reviews like Yelp) to take a look at each deferred maintenance issue you have.

Kelli, Jon is right, keep refining your goals and keep pounding the pavement.

Maybe a few extra bucks on top, but well worth it to have someone out pounding the pavement for you.

Getting out and pounding the pavement is important.