Have you tried putting down compost?
Spread compost before planting the seeds, and blending it with the soil already in place...
Try seeds that do well in shade, and with the amount of shade your getting, you could probably plant anytime during spring or summer, although fall is best.

Your house has a pretty rustic look so hard to get away from it but a soft sage or gray-blue would look nice. If you enlarged the front steps to a semi-circle edged with same bricks as along house it would give a better appearance to front door area extend it enough so you would have area just past the pillars on each side for large pot of flowers or small shrub up on the top step & another on bottom 1 if you wanted them. Can't tell what driveway is. If just dirt, gravel would keep it from being muddy. There are no shrubs, if it is mostly shade need to check out a nursery & see what grows in your area in the shade. It's a nice house that looks like it needs landscaping, a few personal touches!

Your house could look really good with a few changes - you have a nice natural setting to start with. I'd stain the exterior wood siding and use a color as sunnyca suggested. Brighter/darker stains will fade faster so I'd avoid those. Paint the barge board the same color as the roof for a more substantial look. Make the door, door trim, and window trim a contrasting darker color or white, whichever you prefer. A larger porch would look great.

Lay out a curving path to the front door from the driveway - make it at least 3' wide. The path could be bark mulch at first and later do stepping stones or many other choices. Leave about 6' for a planting bed near the house as you don't want to plant within the drip line of the roof.

There can be several reasons for plant failure and the main ones are lack of sunlight, lack of moisture, and poor soil. It's essential to improve the soil before planting or you're just wasting money buying plants. Those large trees are taking all the moisture and nutrients from your soil and have done so for decades so it's almost impossible to grow most plants there. IMO it's too expensive to improve the soil over such a large area so you could limit the beds at first to the area near the house and amend the soil with lots of compost there. There is free compost offered in some areas so check on that first. You could also start making your own but that takes awhile. Otherwise you can buy it in bales or bulk, depending on amount needed, cost, and availability.

If you want to have a lawn over that expanse of yard it will require a lot of expense and work as you'd have to amend the soil, seed, fertilize, and water, water, water. If this were my yard I wouldn't try to grow lawn but would make a few large beds and use ground covers and easy care plants or seed wild flowers. Don't try to do it all in one year but start at the house and work out.

I suggest you drive around and look at some landscaping in other people's yards to learn what style of garden landscape you might like. Take pictures of plants you like and visit a nursery. It might also be helpful for you to join a local gardening club if there is one. Read all you can about gardening - most public libraries have books on landscaping and gardening.

You might check out the link below for the regional forums here at GW. I'm not sure of your climate but perhaps the Southern Gardening forum would be most appropriate. You might find some good ideas for appropriate plants there.

Here is a link that might be useful: regional gardening forums

You buy a barn like house and then don't want it to look like a barn?

Not many houses to choose from and this one was beside my MOM...

Lot of areas of U.S. have very little for sale!! You were lucky to get house close to your mom!! I cook a lot for my 88 & 94 yr old parents & am very glad they are only 3 blocks away. Much easier to keep your mom independent if you are nearby & if you have kids great for the children.

You got some great trees around the house, but what is needed is some more definition of this blank canvas, which could be done with some evergreens shrubs.