You'll smell root rot and see actual rot if it's present. It's just like rotten food. When the drainage is poor the hole needs to be dug larger and you should have a "drain" hole at the bottom of the hole. Typically folks fill a drain with rock. It should go below the hardpan of earth so the water has a place to go. Unless absolutely necessary, your soil should never be amended but there are circumstances where it should be amendment. Never use more than 1/3 amendment to your native soil. A good amendment is sold at home improvement stores and it's called something like "tree and shrub amendment." It has bark fines and peat moss, basically. You should be using a pick axe to do your plantings. Also, when your hole is opened up, you should drive the pick axe all around the sides of the planting hole creating "pockets" for the roots to go into. To drive thru the hard pan you may need more than a pick axe. I'll provide you with a link that will help you. Dax Here is a link that might be useful: Preparing Hardpan For Plantings

btw embo ... that looks like a winter lawn in my MI .... not necessarily underfed ... at this time of year ... what i look for.. is weeds ... and that lawn is prime ... its been cared for in that regard.. which makes me thinks it has also been properly fed ... OP ... do keep in mind ... most conifers.. trees... do not need to be fed ... they are never HUNGRY ... but we insure the soil is fertile.. and take action if need me ... which IMHO ... is rare ... and in fact.. when your plants get going.. and actually put roots out under the lawn ... and if that lawn is fertd.. these things will get more than enough of anything they may need ... finally ... lawn watering.. is rarely proper watering for new transplants... do not rely on such .... though.. once fully established ... they should be rather free range ... refer to watering at the link ... ken https://sites.google.com/site/tnarboretum/Home/planting-a-tree-or-shrub

Were this me I'd change the strategy a bit in order to get more done with the same $. You are purchasing good sized, fairly expensive plants. But much smaller plants could achieve good growth and size within a very few years. I'm in a totally different area but am from the Midwest originally and know that things can grow fast there, too. I have trees that started out as 1-gallon pots that are now in the 15' ht range in 4-5 years. I have shrubs that started at same size and grew to 5' ht. & spread in 4 years. And a Bougainvillea trained upright on a post that is 13' height x 14' spread in the same amount of time .... from cuttings. I'm sure there are plants that could do as well for you and extend your budget substantially. Also, I wish you'd do a comprehensive planting plan before you put anything else in the ground. Dealing with spots here and there, over time, especially if not taking into account the ultimate sizes, you might end up being smothered by your own plants in a maze of sorts. I'd especially be looking into some large shrubs/small trees to screen at a distance since your yard is fairly spacious. Another thing I'd consider is vines on a trellis. Where you are considering screening adjacent to a patio, it seems like a better/cheaper option to me. In some cases I've used a device which I call an extended trellis. It's a series of posts, installed at a spacing like fence posts (every 8' or 10') on which a chain is swagged from each, connecting them. The space below the top chain is filled with some method for guiding vines to grow up to the chain. It could be parallel horizontal wires every 12", stapled from post to post. Or it could be vertical cords that run straight down from chain to stakes in the ground @ 12" intervals. The infill is temporary. If a vine reaches the chain, it can grown on itself & other adjacent vines. In short order, it becomes a solid screen. The overall trellis length can be extended as far as whatever space is available. Annual vines can start things out with quick cover. A permanent perennial vine that will take over for the long term can be installed at the same time. Vines that drape, such as Clematis, are good to use ... not those with woody cantilevering, such as Wisteria. Evergreen trees offer the advantage of winter screening, but they are harder to manipulate to fit situations as they age. I wouldn't put so much weight on them since you're not likely to be spending much time on the patio and in the back yard during much of the winter. Here's a suggestion of an alternative.

Thank you for all the input. Some interesting options I hadn’t considered. I don’t think we can plant a vine on the fence (though it would be beautiful) because it is my neighbors’ fence and they have goats. So anything that grows through or on the fence will be eaten in short order. As far as groundcover/grass goes, we are not trying to grow grass there. The green on the ground you see are just weeds. We are going to clean it all up and mulch everything well once the rest of the plants are in place. We went shopping this weekend and bought cherry laurels, Japanese ligustrum, wax myrtle, cleyera, evergreen and deciduous viburnum, anise, winterberry holly, some more cryptomeria and a couple thuja gg, panicle and macrophylla hydrangea, distyllium, rhododendron, fothergilla, and some perennials and creepers for along the wall. I know it sounds like a lot for the space, but the picture only shows about half of the area we are working on. We also have a lot of other places we can plant things if we find we bought too much.