Here's an interesting page about Tomato planting.
It mentions planting in the North, which is me and Emptybox really.
I'll be trying these ideas anyway as what we do now isn't the answer.
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Before you put your tomato plants in the soil, put one cup of kelp meal and one cup of bone meal into each planting hole to give them a turbocharged start. Kelp is an excellent all-around plant nutrient, which is rich in micronutrients, while bone meal is rich in phosphorus, which promotes flowers and fruits. These are both slow release fertilizers which will provide nutrients over time, without sending plants into shock as might too much chemical fertilizer. Both are also rich in micronutrients. One trick old-time gardeners use is to add Epson salts -- one or two tablespoons per hole -- when transplanting tomatoes. Epson salts add magnesium, an important plant nutrient.
Handle plants gently when transplanting. Any bruising or damage will set them back or leave them vulnerable to viruses or pests. Be careful to keep leaves free of dirt, as many fungi and viruses live in soil.
In the north, both the roots and most of the stem should go into the hole. Only the top leaf cluster should protrude above the ground. Since tomato roots will grow from the stem, the plant will have a larger root structure, which has two advantages: it gives the plant a more stable base, and it allows the plant access to more nutrients. In the south, it's best to keep the same soil level, as the buried stem can be vulnerable to fungus. The longer growing season in the south also lets the root structure reach an optimal size without the deeper planting.
If the plants you are transplanting are tall and leggy, or if you are growing tomatoes in the north, you can use trench planting instead of the traditional hole method. The trench offers two advantages, neither of which is always relevant: you don't have to dig as deep a hole, and the entire length of the plant's root system is in the upper layer of soil, which warms up first in the spring and which usually contains the richest nutrients. Dig a horizontal trench as long as the roots and stem together. Remove all the leaves from the plant with the exception of the top leaf cluster. Lay the plant on its side in the trench and cover the root system and bare stem up to the top leaf cluster with two to three inches of soil mixed with kelp and bone meal. When you've filled in the trench, the part of the plant above ground will be lying on the dirt, but not to worry; it will become vertical within a few sunny days. If you want, you can gently push a rock under it to get it started in the right direction. This is an especially good idea if the weather is likely to be cloudy or rainy.
A third transplanting method involves digging a fairly large, deep hole (a foot wide at the top, tapering to eight inches or so, and up to a foot deep), and then planting the seedling at the bottom of it. As the plant grows, remove lower leaves, and gradually fill in the hole. This method makes maximum use of the tomato's ability to root its stems, but it also puts the seedling in much colder earth than other methods do. To alleviate that problem, dig the holes a week in advance, and put a bottomless milk jug with the top still on in the bottom of each. The jug, acting like a miniature greenhouse, will speed the heating of the soil as well as preventing its collapse into the hole. When you transplant the seedlings, cover them with the jugs, but as soon as day temperatures reach seventy, remove the tops to avoid cooking your plants. Between the hole itself and the jug, a seedling is well-protected from wind, and as the exposed soil warms, it radiates warmth around all sides of the plant. This is an excellent technique to use in barrels and containers, where digging deep holes doesn't involve much labor.