The easiest way to ID weedy grasses is from the inflorescence, the seed producing stalk. Compare your weed to Dallisgrass, you could also try asking on the grasses forum or Name That Plant. Good luck!

I think the easiest way to maintain a large area is to create a woodland environment. Separate the 'woodland' from the 'yard' perhaps with the wall in the picture, or by some sort of border like logs or simply the edge of the lawn, and don't worry too much about maintaining the woods. I am sure you've seen yards that border the woods, and some of them look perfectly manicured despite the fact that nothing is done to maintain the woods. So, it is partly attitude ('those are the woods, this is the yard') and partly a good border between the two that makes your life easier. I would start by by mulching and planting large clumps of a few types of shrubs or small trees. Pick out perhaps three to five types of native woodland shrubs. Get perhaps three to five plants of each type. Plant each type of plant in an informal clump. The clumps should be arranged to look nice, frame in your yard and woodland path, and to not interfere with each other too much (give them the room they need). In general, put taller ones toward the back, smaller ones in front. Mulch the whole area. You can buy shredded bark or find a local tree trimmer or the municipality who shreds branches (power company crews, road maintenance crews etc.) and sometimes get the chips for free. i would use the most natural-looking mulch you can find, so that the woods look as woodsy as possible. in the future, simply leave the leaves that fall. You should probably mulch again in future years to help build ip the soil and supress weeds. I would probably remove a lot of the small plants that are there now. I see a yellow-green groundcover that is probably a sedum, some weeds, I think, and some grass. none of these really fit in a natural woodland, so I wouldn't keep them. As the shrubs grow, the spaces in between you can plant with wildflowers, ferns, etc. Once you get the shrubs growing and a good mulch on the soil, you can take your time (years, if you want) planting wildflowers, and I think you'll enjoy it. I would start with several Flowering Dogwood (Cornus florida) scattered through the woods. I would plant clumps of Cranberry viburnum (tall, put it near the back), American Holly (Also tall), Maybe Gray Dogwood in the sunnier parts of the front, Blueberries (highbush type- most of the blueberries grown for fruit are 'highbush' blueberries that will get four or five feet tall, at least), and perhaps Red chokeberry, or maybe Inkberry holly, which is evergreen. I would make each clump something like 10 ft by ten feet, but an irregular shape. This will fill a lot of space, you'll like the look of the shrubs, and there will be no maintenance - you can simply let them grow once they are planted and watered for the first few months. I think evergreen groundcovers are a pain - weeds often grow through them, it is hard to get leaves out of them, and unless they grow really thick, the look like a poorly maintained planting. Woods, on the other hand, aren't supposed to be maintained and so look fine full of leaves and sticks. Just maintain a path through them and you are fine.

Does it grow like a climber? Kinda looks like AMERICA. If it doesn't climb, then could be something like SEASHELL or SONIA. Without seeing the earlier stage of bloom it's hard to say.

Some thoughts on two projects: One: What is the most practical path from the point of origin at the house to get to your dock -- the path you now use ? Would that path begin at the corner of the house closest to the yard toys -- either a straight or curved path -- until you get to the toys and then from the toys beyond them to the dock? That walk path is where you should begin to create dirt steps about 4'-6' wide by using railroad ties strategically placed across the path as temporary small retaining walls to create level or gently sloping "steps" between the rail road ties -- digging to throw dirt above or below the railroad ties as needed. As you walk, you might take two or three steps on each dirt step you create. As you use the dirt steps you can see what steps work best and what steps need to be adjusted before you invest in blocks or stone for more permanent retaining walls for your grass covered dirt steps). Two: you might consider putting a retaining wall all along the lower point of the yard where you usually cease to mow -- below the hill. Literally dig a deep ditch for a footing/foundation along that line above which you cannot safely mow. You could then put rebar in place and have concrete poured into the ditch (BEFORE before you remove the dirt from below the ditch/concrete wall so the sides of the ditch can serve as a form for your retaining wall) -- before you throw any that dirt from below the ditch to above it. Once your poured concrete has set up, you can add a bock wall atop it, then begin to remove the dirt from below the concrete retaining wall to above the concrete retaining wall, adding other layers of concrete blocks to the wall as you are able to reach it from either above or below until you've achieved a reasonably level area both above and below the wall. You could then face the poured concrete with stone or brick if you choose.. DO make sure the bottom of the ditch you dig is lower that the ground level you want for the lower flatter area below the poured concrete retaining wall.. A ditch dug with a back hoe or other equipment will be wider that what you might dig by hand and take more concrete to fill but with the wider concrete wall you're pouring, you're building strength into your retaining wall. Do post some after pics to show us what you've done.