Do you own it or are you coming in as a contractor? What does the owner like? What climate/soil is it?

Hi Homebound, your home is similar to a relative's home in Michigan. I am no expert, just a homeowner having some time to browse this morning. A patio over the enclave would look nice especially if it can have an A-shape roof with exposed beams and extends at an angle not parallel to either side of the L shape walls. Level the entire enclave step with stones or stamped concrete with steps leading up to it. It would make an inviting entry. With flowers and landscaping on both side and a winding path leading to it, add lighting, whewww! A larger bedroom window would be nice, better proportion to the wall. Some sort of frame color (other than white) that you like or something that matches the house color would be nice. Forest green? Add a nice long flower boxes under or better yet, add a planted bed of flowers along the wall and it is curb appeal galore! May be nice to spruce up the wall with good quality black coach lamps of some sort, it makes for nice lighting at night and nice visual appeal in the day. Sorry, I am just day dreaming :-). Have fun fixing it all up!

I agree with you 150% about the driveway!!! We are hoping for a "phased" approach to the whole transformation considering we don't have a ton of money to throw into it at one time. I think maybe I should just tell you "dark blue" for the paint color! I can't thank you enough for this - I am assuming you are a designer?

So if I’m understanding what you are looking for, not sure what you mean by a hammock, this is what I suggest. For the divider wall, you could get a decorative panel or an ikea divider/bookcase. That would give you a little separation to create your other seating area. Possibly do a graphic wallcovering mural along that back wall to unite the two spaces. You can get peel and stick now that is easily removed.