I like the cypresses.

If you want deep beds, let's spend some time discussing scale. Deep beds need tall plants, otherwise it looks like Godzilla in the village. You are looking down at an expanse of miniature. What you have now is not miniature, and can work as a good backdrop to smaller plants.

Continuing the discussion of scale, if you want a shade tree PLANT A SHADE TREE!!! Don't plant some miniature model of a shade tree which will then take up the space the real shade tree should occupy. That isn't a small house, and it would be complimented by a tree with the potential to overtop it in someone's lifetime.

I think I have an idea of where you want to go with this, and the key is going to be thinking big. Deep beds, large plants, and a willingness to dive in.

BTW, Don Juan is going to need a serious spray program.

Thank you for your thoughtful reply, @mad_gallica! Totally agree about scale of trees. I was second guessing myself with the ornamental trees, but I will go for something big. We have a big white oak on the side of the house, so I know oaks do well here.

My problem with the cypresses might just be my own taste-- they feel kind of goofy and shaggy and undignified, but might bother me less if they were the backdrop to other perrenials. I am envisioning something with a contrast of clipped shapes and then looser planting-- maybe my perennials go in front of the cypresses with smaller box balls in front?

And good tip about the Don Juan -- I have gotten lucky so far with all my roses so far and have gotten away with hand-picking insects and no black spot.

I would not stick ball boxes in front of your existing shrubs. Nor would I remove the shrubs to replace with balls. I'd move the tree to the right of the steps. The best way to do that is to cut the roots in a semi-circle in the fall and then do the other half in the spring.

Moss phlox planted with alliums would look really good flanking the path. Moss phlox is, I think, evergreen. It blooms in the spring. At least for me, it has no diseases and looks good all the time.

Get some alliums that bloom in the summer. I have alliums growing in my moss phlox.

I like the cypresses and think they could look cool incorporated as a layer with some deciduous shrubs (panicle or aborescens hydrangeas would look nice!) and perennials in front. The cypresses add a soft rounded shape to the future flower bed which would let you play with spiky and conical shaped plants in front. There’s some more info on that concept here: https://www.prettypurpledoor.com/garden-design-principles/ I would definitely move that tree though. I think that one change will open up your porch and front of your house a lot.

It’s all past it’s prime. And I can’t stop seeing a giant kudzu covered horse to the back left of the house.

I don't think heavy foundation landscaping is appropriate for an 1870's farm house. Please research the period and choose a style that suits your historic home.

I have a book, 'Gardens of the Gilded Age', that is a study of contemporary photographs of 19th century gardens and homegrounds. The thesis is that although the architecture survives, almost no plantings have, so few people really know what the landscaping was supposed to look like. I was hoping to find excerpts online, since I think it is very interesting, and definitely relevant to this discussion. All the photographs, like the author, are from New York state, but from the 1870's to 1890's, it covers a lot of residential ground. There are pictures of farmhouses, suburban developments, estate grounds, and small urban gardens. By current standards, most examples are overgrown, though not overplanted. The examples of formal gardens are from the earliest pictures. Later ones are naturalistic and Romantic. There is a 'wildness' to them that you don't see today.