I realize it's an old post, but before spending a lot of time and effort on prettying up the landscaping, you might first consider installing a new roof (replacing what's there now) on the house--the existing shingles look a bit distressed, even with the poor resolution and scale of the photo.
I've never been fond of being a slave to my yard. The vicious cycle of mowing/watering/fertilizing never did much for me, and the older I get, the less appeal it has. I've been mowing a 1.5 acre parcel (in 3 different states) with a John Deere tractor/54" mower off and on for the last 12 years, and it hasn't gotten any more fun as the years pass by. I'd much rather be tinkering out in my shop.
If I was looking at some landscaping ideas for the subject yard, high on the list would be some colorful, low-growing ground cover. The kind that doesn't need food, water or mowing--just plant it and forget it.