OK, you have the plants & you need to get them in the ground. Raspberries take up quite a lot of room in a sunny area. They can get out of control quickly & grow long swaying boughs. I tried growing 4 in about 10 ft. by 3 ft.area, not nearly enough space & not full sun so I ended up taking them out after a few years. Strawberries like a lot of sun but can probably take a little shade(in So. Ca. anyway) don't bury them deeper than they are in pot. They spread by runners next summer so figure out your bed so it is easy to get to plants & from all sides to pick berries. Lilies spread so if you are tied up with kids or getting older might want them somewhere so if they multiply it won't ruin your garden if you don't get to them each year-they like lot of sun.They are most attractive when several of 1 color are clumped together. Iris don't like being messed with until divided. Lily of Valley like lots of shade as do most Hostas. Sort out your plants by area they need to be in,then arrange them in their pots until they look right, keep your veggies separate from other plants & try to keep your herbs in a bed by themselves, chives, oregano, onions,etc, they get messy & might put parsley around outside edge of this bed to make it more interesting. Get some graph paper & start planning on paper so you know where you will have trees how much shade they are going to give & if they can have shade plants under them. Get your sunny areas figured out & that will be area for veggies,berries, herbs,if you are planting corn,peas, green beans, squash they take up a lot of room so you will have to cut back on shade. If there is nothing behind garage & a space back there in shade you can make that your lily of valley area & break it up bit with couple of hostas. You don't want your garden & yard so much work you don't get to enjoy it. Digging out the lawn to put all this in will be lot of work so have to make it more manageable.If you want paths you need to include them. Need place to sit & relax & have friends over so you can enjoy fruits of your labors.If your library has Birds & Bloom magazines, there was lovely evolved garden in there some months ago. All gardens evolve as years go by, you find what works for you. The perfect spot at your neighbor's 2 doors down may get you O results at your place so lot of it is trial & error.I love rhubarb, planted it & it was going crazy,hanging over in lawn so I moved it,never have found a place that works since. I had planted a lovely peace rose there I don't have any rhubarb now. It doesn't like wet feet. So you may have to move plants that aren't happy anyway no matter how you plan it out. Good Luck!

Have you considered Viking Queen? It comes highly recommended to me, specifically as a "Northern" gardener (and is a very well regarded descendant of New Dawn, from which Awakening sported), and when funds make themselves available (don't ask) I have a spot for it. Another one that intrigues me (but I've been told is too upright for the 3' high cast iron fence it is my lot to work with) is Inspiration (another New Dawn descendant). I will freely confess that I have not grown it and do not know whether it is easy to grow, or a disease-ridden chore (although obviously it can be found at the Brooklyn Botanic Garden). New Dawn has been used extensively in the breeding of other climbing roses. Its flowers are quite as amazing as Awakening's, except they are more like a doubled "hybrid tea" flower than the quartered, very heavily doubled flower characteristic of Awakening (which, if I understand correctly, is otherwise identical to New Dawn).

I have the same situation, split rail w/ wire fencing on 2 sides of the back yard (record north is right at the corner), w/ the neighbors' privacy fence to the s/w side & the house & side fences along the s/e. I have alot of large maples, oak, beech, pine in my yard & also large trees in the park to the n/w & my other neighbors' yard n/e. What has been successful so far-at the back, which borders the park & has 5 white pines, limbed up, & a maple (basically a western exposure, but some huge oaks & cedar at the park providing additional shade) I've planted nandina, pieris japonica, viburnam, J. maples-Scolopendrifolium, Spring Delight, Garnet, & Viridis in the N. corner. I also have hydrangeas-oakleaf, Nikko, Lady in Red, blueberries, itea, fargesia robusta, & camellias. The soil under the pines is rock hard clay, dry & shaded. I try to keep the newly planted things watered, but we had a brutally hot summer. What didn't make it-a Japanese black pine, a camellia that was attacked by a squirrel. I planted lots of heucheras around the Jmaples, I hope some will return next spring. I tried hops along the fence, but they didn't make it (I think I planted too late), but I hope the passionflower that was vigorous last year will return. On the n/e side which borders my neighbors yard, which is lovely, but mostly large old trees, lawn, & ivy, under the shade of an enormous maple-which has terrible soil, it's clay, dry, rocky-I've tried alot of shady perennials. I'm adding compost to the bed as fast as I can make it. Right now, it's mostly variegated & plain J.pachysandra, epimediums, hostas, hellebores, violets, rohdea japonica, a variegated sambucus (I had 2, 1 died), heucheras, & a gorgeous 'Snow Flurry' camellia. My experience so far, (I've been here 2.5 years)is that it's challenging but possible to garden in less than ideal conditions, & my garden gives me a great deal of pleasure...

What is the purpose of planting along the outside face of the fence? Since the fence supplies any need for privacy, I would assume it is just for a decorative element? 5' is pretty narrow for much woody plant material - even most fastigiate plants will eventually fill the area rapidly and in time could extend into the roadway. You could of course prune to keep in size but a bit of a PITA to need to do that routinely on the exterior of the property. Columnar arborvitae like Thuja occidentalis 'Smaragd' would work but extremely common and vastly boring. And really no need for something of that mature height. Since you don't really need the height, I'd suggest one of three alternatives: 1) leave the lawn as is (least interesting but also with very low maintenance). 2) Replace lawn with groundcover, interspersing a landscape boulder or two as desired. 3) Plant with a selection of taller, upright ornamental grasses (Miscanthus, Panicum). These will offer a lot of seasonal interest throughout the year and require minimal maintenance. You could also toss in a couple of boulders as well but do avoid the repetition of three grasses, one boulder, three grasses, etc.