The best thing to do is to consult a local garden center/landscaping designer for an overall plan. While it can be expensive, a lot of plans can be implemented over several years to spread out the cost. A landscape designer is the best person to integrate hardscaping and plantings. For better advice here, tell us what zone you're in or the nearest large metro so people know what climate you're working with. Your grass is in poor shape. It is a lot of work to maintain a large lawn. How much lawn do you want? Do you have too much right now? You could let some of it return to nature to cut down on maintenance.

Thanks so much for the info. I’m in Connecticut. 5b 6a zone. The grass is terrible. Its all weed. The rest of the property is woods so we do t have to mow and the only large flat portion on the side is septic leach field. I want to leave that as is no need for lawn. I wouldn’t mind wildflowers etc. The side of the house is a big slope too, so pretty unusable. We have a big unusable property. Not complaining though because we know we are lucky to have it. Didn’t add any pics of the rest of the property because as I said I know it’s a huge endeavor. I think that even though we are flag lot ( behind the other property) we are lucky because it’s a wooded area. I want to make this front portion more usable and pretty .In whatever capacity. The wilderness is just so close to us that creepy crawlers are everywhere haha. Hoping fixing it up may help.

Some idea

Wow, thank you so much!! How did you do that? Great idea

Or with fence or without

What sort of creepy crawlers concern you? Ticks? Snakes?

We have ticks, tons of carpenter ants, spider - every species of spider , frogs, caterpillars all over the porch, carpenter bees, wasps. Haven’t seen any snakes but I’m sure they are here. Oh and we have bears and bobcats, though they wouldn’t be considered creepy crawlers haha. We really feel like we are the visitors In their home.

If you border woodland, you have a special responsibility to not plant anything that will invade the natural area. Choise all of your plants with that in mind.

@kitasei2 yes definitely :)

Any plantings will attract insects which you aren't keen about. I'm imagining a landscape similar to Celery's first rendering which uses a variety of hardscape features and minimal plantings. Few plantings also leaves more play space for the kiddos inside the fenced area.