And it might be that the large bushes next to the house need to be taken out completely, but I’d prune first and then assess.

The bush on the right looks like a yew. They can be hard pruned back to get a good size and shape even if they look bare for awhile. It looks like the bush on the right can come down quite a bit, although I don't know what it is. Actually it looks like there is more than one bush. Looks like there are some blooms near the ground. Get really good pruners and a good pair of shears to make your job easier and enjoyable. Do not use electric hedgers.

Mulch the beds. If you put several layers of newsprint down before you mulch, you won't have to weed.

Get a pro after that tree in front. You can probably handle the other two bushes yourself. IMO, a new design for your landscaping is in order. Spend time to plan it out, including a new walk straight out to the street, improved lawn and a new perspective on landscape plants. You can add in a few plants that give a nod to the former owner if you want.

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As for the lawn, knowing your zone is meaningless. Zone 5 runs from Maine to the Aleutians. We need the name of the town where you live. That tells us more about your soil and climate than the USDA zone does.

I'm going to assume you're going to trim that tree up so people can walk under it and stand upright. It will still cast so much shade that only fescue will grow under it. You could have Kentucky bluegrass in the sunlight, but only fescue will work under that much shade.

Now is not a good time to seed, but the alternative is weeds. I would encourage you to understand that seeding now is a waste of time, effort, money, and hope. If you spent the effort, you're going to be disappointed in July when it is all weeds, anyway. Suck it up for now. You can fix it right in August. Seeding in the fall gives the new grass time to mature before the summer heat.

Fill any holes you have, but don't use too much soil. Don't topdress 1/4-inch just because the yard is doing poorly. Soil is easy to fix.

Spot spray Weed-b-Gon NOW to take care of the dandelions and other broadleaf weeds. Two weeks ago would have been better, but now is the next best time. That gives you time to evaluate the effectiveness before the summer heat hits when it's too warm to spray.

Set your mower to the highest setting for the rest of the season. Tall grass is much healthier than short grass. It also helps prevent weed invasions.

I would fertilize now with an organic fertilizer. If you want to use a synthetic fertilizer like Scott's, then wait until Memorial Day - no earlier.

Summer watering is most important. The deep and infrequent is the mantra for watering. Deep means 1 inch all at one time. With a lawn on a slope like yours, it will have to be done slowly to prevent runoff. You can measure 1 inch by putting cat food or tuna cans around the yard. Then turn on the sprinklers and time how long it takes to fill all the cans. That will be your watering time from now on. As for frequency, with temps lower than 70, deep water once per month. Mother Nature usually takes care of that for you. With temps between 70 and 80, water once every 3 weeks. With temps between 80 and 90, water once every 2 weeks. With temps in the 90s, water once per week. Use this schedule as a guide, not gospel. The important thing is DEEP watering and never water every day (or 2 or 3). Deep watering makes this all possible. My watering time with my oscillator sprinkler on full sweep is 8 hours. That is pretty slow, but runoff can still happen. The time depends on your water pressure, hoses, sprinklers, etc.

If you get the watering and mowing right, it's going to look much better for the rest of the season. Come August, write back to the lawn forum for advice on reseeding.

While it may seem disheartening at first, I wouldn't be crying too hard. A lot of plants seem like they're in wrong places, and in some cases, especially on account of their size. Life would be easier (less maintenance) if plants didn't need tons of trimming just to keep them under control. Better to place big plants where they have the space to grow to their size.

Like for most homes, this one cold benefit by widening the step and landing to the full width of the porch opening. Carry this on by widening the walk to 4', or even 5'. Personally, I think the house could benefit greatly from having the porch posts replaced with some smartly decorative, heavy wooden posts and a new railing system ... one that is tastefully simple. I would reorganize the whole foundation planting. There's a possibility of creating a quarter-circle landscape bed where the city walk meets the street. It could have a small, multi-trunk tree, groundcover and all those daffodils spread throughout the yard (none of that shown). The blooming tree next to the street desperately needs cleaning up.

Any updates to the house structure should come first. You don't want to trample / disturb newly installed landscaping.

Would suggest a start over on this one and as Decoenthusiast said hire a pro to help you out - if not a landscape architect then a landscaper who has design abilities and a good portfolio of work that he can show you. It's a nice looking house and with some good landscaping will be a great place. Good luck!

I have to agree since it does not sound like you are a gardener you need some real help. Roses are lovely if you love them and the work involved and in zone 5 they take a lot more work . Talk to landscape designer to get a plan and work toward it over the next couple of years if you can’t do it all at one time. As for the grass once quack grass gets in there you need a complete redo since anything that will kill the quack grass will also kill the good grass . I like all the advice from Deco . This acn be a really pretty place but it will take work and if you ever need to rent out again get a gardener to keep it up. That front walk needs to go from the street to the front door.