At the Organic Growers School Conference, Ira Wallace and I co-presented a half-day workshop (twice!). I uploaded the slides as a pdf on SlideShare.net, and here they are.
Those who start early in “spring” (late winter) might get earlier crops, but when is it worth it?
Some crops are just not going to thrive if you start too soon: cucumbers, peppers, and even tomatoes, for example. Make sure you can provide conditions that meet the minimum temperature requirements for these tender crops. See my book Sustainable Market Farming, for all the details. We used to start these tender crops earlier than we do now. March conditions have become more unreliable, often colder.
If you already have a place to grow protected crops, or you are experienced with rowcover and have plenty on hand, then the signs are good. Crops can be started earlier in a greenhouse or hoophouse (or even on a kitchen windowsill) than you can sow them outdoors. When the plants reach a good size, harden them off and then plant them out in a mild spell, with rowcover for the first couple of weeks. Pay close attention to weather forecasts.

Photo Twin Oaks Community
“Hardening off” is a process of acclimating your plants to colder, brighter, breezier conditions, so that they won’t suffer when they are transplanted. If you have only a small number of plants, or of flats, you could actually bring them back indoors every night and set them out every morning for 10-14 days. Growers with lots of crops to harden off will make use of a coldframe. Depending on the actual temperature (or the expected night-time low) we might leave our plants uncovered, use rowcover, top the rowcover with transparent lids (“lights”) , and if it’s going to be really cold, quilted covers, weighted down with wood beams if it is the least bit windy.

After two weeks of hardening off, look for a few days of mild, calm weather to plant them out in the garden. Water the plants well the day before transplanting, and again one hour before transplanting. This allows the cells of the plants to fill up with water, enough to tide them over the period of “transplant shock”.
Even the most skillful of us end up doing some damage to the roots of transplants, and that means the plants have to regrow some lateral roots and root hairs before they can pull in water at the rate they were doing before your ministrations. As you transplant, avoid touching the roots of the plants. Our fingers damage the root hairs.

Photo Kathryn Simmons
A way to minimize the root damage is to use soil blocks or Winstrip plug flats. These methods are more expensive in time or money than open flats or bare root transplants, but they allow the roots to get “air-pruned” as they grow. When the roots reach the air at the edges of the blocks, or at the vertical slits on the sides of the Winstrip cells, they stop growing, rather than circle around the cell, causing the plant to get root bound. Secondly, these tools work by helping the roots and compost form a coherent block, one that holds together as you pop it into the hole you create in the soil.
Speedling flats are styrofoam flats with tapered cells, and it is possible to slide the plugs out (or gently pull them out) with little damage. Regular cell packs (4-packs, 6-packs etc) can be encouraged to release their transplants by squeezing them at the base of a cell, while holding the pack sideways. Then spread your fingers over the compost around the pant, invert the pack and hopefully the plant and its compost stays as an item, with your fingers either side of the stem.

Photo Denny Ray McElya
Hold the plant with one hand by a seed leaf, or if you have to, by the stem. The seed leaves are disposable, stems and roots are not! Hold the plant at the right height, usually with all the stem below the leaves in the ground and all the leaves above ground. Once the plant is in the ground at the right height, hold it there and use the other hand (maybe with a trowel) to push in soil to fill the hole. Firm the soil down quite well, pulling in more soil as needed to leave a level surface. You don’t want the plant to be in a divot, where water can accumulate.
About the degree of firmness: you are aiming to make good contact between the soil and the plant roots, so the roots are not in air pockets, but rather can suck in water from the between soil particles. Don’t firm so hard that you expel the air from the soil and make what feels like concrete the next day. With cabbages, I was taught to firm enough so that if you then grasp a leaf and pull, the leaf tears off, rather than pulling up the whole plant.
Plant for 20-30 minutes, then pause and water in each of the new transplants by hand. Some people will bring a watering can along the row and water each one, one at a time. I prefer to do little batches. At the end of you transplanting session, water the whole row or bed again. try to avoid having piles or dishpans of plants with roots exposed to the air. Definitely don’t take a tea break if you have exposed plants.
Cover with rowcover if needed, or shadecloth if the weather is very bright and sunny. This will just be for a few weeks, helping the plants recover from the transplant shock, and biding time while spring warms up.
If it doesn’t rain, water again the next day (day 2), then on days 4 and 6, then twice a week, then once a week forever after that, until harvest is completed.

Photo Wren Vile