Thank you for your feedback. We recently purchased the home and we have a lot of work to do! It is on acreage, that is the main reason we bought it :)

I will definitely take down the planters and try to incorporate into the new landscape.

I am at a loss for what to do for a walkway in place of the pavers. My boyfriend wants to put a flat concrete patio that butts up to the porch and then a couple wooden steps down.

I also like your idea of doing something with the railing to make it less noticeable.

@Amber Jo consider a stamped concrete driveway, walkway, and patio with radiant heating so you never have to shovel as long as you have power. You won't be sorry. 

https://www.warmzone.com/snow-melting/

Is there any chance it could be in the budget to double the size of the covered porch? Remove the pavers and extend the porch floor out, carry the roof over it. I would add a low peak to that roof, Then you only have a flat walkway to the driveway for deliveries and you have a very useable and welcoming outdoor space (that you will never need to shovel). I think it would look just fine wth the rest of the house.

I've never lived in Wisconsin so maybe what I'm proposing is impractical or too expsensive. But I do live wher it is icy in winter and I think it is important to be able to quickly clear a safe walkway to access your front door, so when you create a new walkway, if you can afford radiant heating, great but otherwise try to minmize steps, include railings and make the walking path easy to shovel. Make that a priority in the design and choice of materials.

We replaced our slate walkway with TechnoBloc pavers and covered out concrtete steps in their matching slabs. Easy to shovel or use the snowblower on. I live in Western Massachusetts so we get pretty cold although probably not as bad as Wisconsin.

You have 2 areas for planting on either side of the steps. I'd clear out the clutter and weeds and put in some shrubs. Broadleaf evergreens, unless you have full sun. Even a bunch of boring yews would be better than what you have. Then, I'd clear up the gravel sort-of path to the right.

I kind of live the pavers, I'd weed them.

Unless you want ever greens, I'd do a mix of Clethra, Itea, Fothergillia, and winterberry, assuming you have the space. Shrubs are low-maintenance. You could do blueberries or currants and get some berries.

Before you plant berries, ask the neighbors what kind of animals hang out in that part of Wisconsin.

I think the house is kind of non descript so what sort of style do your want? I doa gree about the wildlife it for sure needs thinking about when planting. I woudl not do a aptio out front when you have ahuge area at the rear for outdoor entertaining. Rip out all that stuff you are planning and IMO that bay window does not work on that house.. Yes the porch being bigger would be very appropriate to the house but a big expense to do right . I would finish the interior before doing anything on the exterior so slow down and finish the inside taht will drive the exterior and give you the freedom to put windows where you want them too then you design the outside.

While you are thinking about the walkway, think about having full ramp access to get to the interior lower level of the house. You may not need it, but sooner or later you will have a relative who will. It could be in front, garage or back.

I wonder if you could have a full concrete sloped walkway from the driveway up to the porch. I don’t know if that would make it more dangerous in snow though. Probably depends on the slope.

Also the front door bugs me. That sidelight on the left. I’m not sure what you could do with that.

Aside from weeding/cleaning up, I wouldn't be in a big hurry to do stuff. You are talking about fairly expensive projects that you want to get reasonably right the first time.

Is the property bug free enough that outdoor living without screens is pleasant? If it isn't, then decks and patios are just wastes of money.

If the front of the house where you want to do your outdoor living? It looks like privacy isn't an issue, but orientation might be. Is house shade a plus or a minus? There isn't a right or wrong answer, just which you prefer. Again, if you find out the back of the house is more pleasant, then a patio on the front is another waste of money.

Wooden steps can be very, very slippery.

To address some questions/comments.

Radiant heat sounds wonderful as winters are snowy and icy. We already have radiant heat in our house. I wonder how difficult it would be to extend out to the walkway/patio.

I love the idea of extending the porch and adding a gable. I am not sure if it is in the budget currently as we are working on updating the inside of the house too.

We do have animals of ALL kinds. We have bears, deer, bobcats, coyotes, etc. Our 40 acres is covered in berries, apple trees, etc. But you are correct, I am not sure if I want them close to my front door.

Bugs are typically not much of an issue. We sit outside on our open porch quite frequently. Ideally, I would like the large outdoor entertaining area to be out back, but I do like the small porch in the front with the walkway to connect to the driveway.

My main focus on the house right now is the interior. However, these pavers are starting to rock back and forth and crumble. It is becoming a safety issue and I really need to do something with it sooner than later.

Thank you for all your feedback. I will probably incorporate many of the ideas somehow.

The porch walls need to be the same color as the siding on the rest of the house. The dark color makes the porch railings to prominent. A concrete walk would look much nicer than the pavers. Are the steps pavers, too? I agree with Mad about wooden steps being very slippery. Just cleaning up and removing hanging baskets, weeds, etc. would make the whole area look better.

The soil in the raised beds looks like it needs to be improved. I can see those beds planted with evergreen shrubs in front of the porch and the rest planted with either annuals or perennials. You may want to just cover that area with a good, thick layer of mulch until Spring, and make a decision then.

Com eback whaen the interior is done then we can see any changes in widows even entry space Get the indise righ then do the exterior . I see little use for heating a concrete pation in the winter so let that be a maybe improvement but honestly why do that at all.

Radiant heat is not difficult to extend. Call the company and they will guide you through the process. Warmzone has great tech support for your contractor.

I love it so I don't have to worry about ice or snow in winter. No more shoveling, no more falling, no more worrying about others falling.

My driveway and front walk have radiant heat, so I never have to shovel. It was a deal breaker after falling on ice one year three times. We either got radiant heat or we were moving.

I would consider staining those little bits of tan stone to match your siding. They sort of look like something has been torn off.

Here are a few ideas: