For some reason that's upside down.

It is a hard question to answer without site specific information about the soil conditions and the amount of sun the specific area receives. A place like Lowes generally doesn't have the best selection of plants in my experience. I suggest you go to a place like Weston Nurseries in Hopkinton. It isn't that far from Needham. They will have a lot of options. And I am sure they can answer specific questions about winter color and site specific needs for different plants.

If you are in Needham, I'd suggest you go to the Garden in the Woods in Natick. They have a large selection of Native plants, which are more "Earth Friendly".

The main thing to know if you are planting in New England is keep track of the climate zones. We are Zone 6. However, big box stores have been known to sell things that don't really grow in this climate.

The obvious thing to plant for winter interest is Holly. I find it transplants easily...even I can do it with my "brown thumb". (I tend to plant things at my parents when I visit, but they can't really care for the things I plant. Holly is one of the few things that survives my "plant and neglect" strategy.) However, I don't think Lowes has it right now...they only seem to have it certain seasons.

Rhododendron keeps it's leaves all year and does well around here...and has large flowers. Same for some varieties of Azalea.

Hydrangea do well and are beautiful, but don't look good in the winter.

As far as whether the soil has to be amended, it's hard to say without seeing it. Is it hard? Sandy? New England soil tends to be full of rocks, acidic, with lots of sand or clay. However, the grass seems to be in decent shape, so any of the pretty hearty plants I suggested above would PROBABLY do fine without amending the soil.

Here is a link that might be useful: Garden in the Woods

Yes, I think Lowe's will have some evergreen plants, although maybe not the best ones. If that's as far as you can get, don't worry about it.

Does this area get a lot of salt when the street is plowed by the town? That's probably not something you need to worry about in the southwest.

Also, low shrubs *might* be plowed over by a town employee who can't see them, so you might want to be careful where you place them, or stick to super tough groundcovers, like vinca minor, under the taller plants. Vinca is evergreen.

Here in the cold climate areas, we talk more about 'winter interest' than 'winter color'. Evergreens DO provide some green, but other than that they aren't the most interesting things in the winter (in my humbe opinion!). Nicely shaped deciduous woody plants have a charm of their own, and you can look for plants like winterberry that will be full of birds when their berries are ripe - a real treat in an otherwise bleak landscape.

After planting, you might want to set up a soaker hose and a timer, if your brother's not a gardener. Summer heat can be tough on plants the first year or two.

Good luck with your project - hope you'll let us know how it goes.