Would you consider removing every other yew then cutting back the remainder? You need foundation evergreens and yews can take a lot of pruning. The heavy "eyebrow" look needs to go but a few yews dotted along with perennial flowers fronting them may work.

I'd reshape the yews into 'clouds'. The only reason they are boxy is because somebody made them that way. If you don't like it, make them into something else. Be Imaginative! Artistic! If it doesn't work, they are yews. You don't (usually) shave your head because you've gotten a bad haircut. You let it grow a bit, then try another haircut.

If you let the yews get a bit taller, you can put smaller flowering shrubs, perennials, bulbs, annuals, planters, garden art - whatever - in front of them. That's how you get the best of both worlds. The yews do the heavy lifting during the winter, but provide a good backdrop during the growing season.

How this works in the north is that first you remove the yews, and plant trendy flowering shrubs. Then after a few winters of nothingness, you pull the flowering shrubs and replant with evergreens. What we are trying to get you to do is avoid the middle steps, and go straight from evergreens to evergreen. Much easier, cheaper, and less stressful.

Or do you envision a prairie type lsndscape, which would honor the mid century modern provensnce of the house and contemporary landscape design?

If you will be replacing siding, workers will need access. If you plant new and expensive shrubs or evergreen trees, they may get broken or cut back so workers can do their job. Maybe work with what you have per the above at least until siding is done.

What they said about the yews 👆. Keep a few.

As for the planting beds, they are too small measured from the yard to the house. On the right side of the door, see that strip of grass between the yews and the sidewalk? That strip shouldn’t be there. The bed should come out to the walk, which will give you room to add interesting flowering perennials. And swoop the far right end around the corner of the house, if there is room. Then make the bed on the left the same size.

Yes, you definitely need a new portico. Google pictures of entry porticos, or search Houzz for pictures. It doesn’t have to be large, as your house is fairly small, but it should be more substantial than it is now. Obviously it will cost you some bucks but it will make a tremendous difference in the appearance of your house.

Here are my suggestions. Perhaps you can integrate some of your yews into the landscaping. I would start with planning a nice walkway to the driveway and work the flowerbeds around that. Remove that roof overhang and build a proper portico. Here's a visual...

You can move yews. I might put them in the back of the house, if you don't have foundation plantings there, or along the lot line.

I would not stick a stupid double gable on a new porch. I'd paint your door before replacing the porch.

If you're in Wisconsin, you probably want some broadleaved evergreens in your mix. Or you could do prairie. I'd go to the Olbrich Botanical Garden in Madison for some ideas, unless you're closer to the Chicago Botanical garden (which is bigger, but I haven't been there). I'd imagine you can find people happy to give some general advice, particularly if you go when it's not that busy.