Answer: Everbearing strawberries are the best for a strawberry barrell, since you are putting so much effort into the ornamental aspect of the project, you should get a more consistent edible reward!
When I plant them I simply fill them up as I go...add a little soil, put a plant or two in the holes, move up to the next layer until I have filled the whole barrel, and then plant the top of the pot. To keep soil from sifting out the holes, use sphagnum moss used in hanging planters and pack this gently around the plant.
I like to use potting soil that has been mixed with compost. Here is one of my favorite tips: Before planting, get a piece of PVC pipe about 2" in diameter, cut it to be about 1" taller than the soil line of your pot and drill small holes in it all along the length (perhaps 12-15 total). Place this in the center of the pot before you plant, be sure you have a lip sticking out of the soil at about 1" in height. Fill the tube with peastone or gravel. This creates a very efficient watering "tube" to insure all the plants get ample water all the way down the pot...you simply pour your water down the tube. Keep the soil moist, but not saturated, and feed the plants with a mild plant food (such a seaweed or fish-based liquid fertilizer) in the spring and during fruiting period. Place the pot in full sun, and protect the plants from frost. As the young plants are getting established, picking off their first round of buds can help them put energy into rooting. Be sure to keep an eye out for birdies....they adore strawberries!
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