If entertaining is a must, you should consider (if in budget) an outdoor kitchen area. A houzz search for outdoor kitchens should bring you some ideas. As far as plantings for your region, your local greenhouse or landscape pro should be able to design or recommend plantings for your space. I've attached a few pictures of one I designed/built to give you an idea. More pics on my profile page if interested.

It all depends on the budget and if you are going a phased or all at once creation. Very envious of a blank/flat slate of your yard!

@greg- what would your end result look like? I can figure out the order but I need help sectioning the space

Again, if budget allows, having a set of boots on the ground will give you some ideas on the best use of your space. Contact a few local landscape pros to help with your design plans and construction.

Hypothetically speaking, if budget doesn't allow for professional landscapers, what's the next best option?

For me... I would extend the size of the current deck, out another 5' and width of the house. Put a roof on it with no ceiling and have fans. As Twisted stated incorporate an outdoor kitchen. i would put in a fireplace either at the end, will close in the deck, or on one of the sides to keep the deck open. The yard would have a kid and animal friendly water feature. large rocks/boulders stacked with a waterfall. Base of it would be river stone so there is no open pool. This feature could be at the end of your deck so it is a conversation piece while entertaining. two or more sets of stairs from the deck to the yard. One with a path to a more private cottage sitting area with tall grasses, flowering shrubs, and an accent tree or two.
Use the back of the yard for a play set, club house/shed (single building, two sides) and grass/lawn area for Fido.
You could add in a few mounded gardens and plant with so many different things... that is how i would start. :)

Goodness gracious! What do you think of a firepit patio and seating area in the middle of the yard? As far as all of your suggestions (thank you!!) are you art savvy and could give a drawing? Stick figure is perfect. The fence has 3 entrances, each corner and the very back.

I'd go for something like this .. as far as form .. lots of curves and some raised beds and walls for interest. Maybe put a similar kind of structure to the left of your garden and move a little dirt around to increase the height where your neighbours buildings are directly in your line of vision. That way, your taller (fast growing) trees will take less time to hide them from view and give you privacy.

Obviously, the attached pic is not in your geographic area, so plantings for such a scheme would be rather different ... but I think the use of space would work well on your lot.

http://images.landscapingnetwork.com/pictures/images/636x510Max/backyard-landscaping_1/backyard-xeriscape-garden-pergola-fireplace-red-twig-studio_8862.jpg

Plants, paths, arches and hidden areas ......

mflohelp, Hypothetically speaking, if your budget doesn't allow for professional landscapers, your next best option is to look online for images of gardens that appeal to you and appear to have similar dimensions (or could be adapted to your space) Draw up a rough plan .. and then get out there with a long length of garden hose, make your curves and walkways, (photographing your layout as you go) and using coloured chalk spray to mark them on the ground. Loads of gardening websites will give you details of the plants and trees that grow well in your area and many show gardens with full planting schemes. You'll need to research the growing habits of the various plants that appeal to you ... a local garden center will give you a lot of info, for free. I'd be thrilled if I had that much dirt to play in !!

you're in an area of the country where you can have a vegetable garden almost year round. I would plan for a garden since you have tons of space. I would be careful not to do too much landscaping all at once. maybe just do the fire and cooking area and then plan your gardens. have you thought about a pergola? wisteria? roses? flowering trees? fruit trees? grape vines? you can certainly peruse on Houzz, but sometimes the library is a great source of ideas. Ours has tons of wonderful gardening and landscaping books. I check them out over winter just to cheer myself up :) I looked through one on Winterthur, the Dupont estate..they had a special section for the children..you never know what you might find that will inspire you.

totally go for something simple and plant up from there... from the Houzz library