If you carve a X through the skin before boiling, the skin will begin peeling away from that spot first and will make the tomato easier to peel. If you care about the state of the tomato after you skin it, make sure to keep the cut shallow -- only cut through the skin.
After boiling(You shouldn't actually boil them unless that's what the dish calls for, a minute in boiling water is enough), immediately submerging them into ice water makes them even easier to peel.
If you boil them for more than a few seconds, you'll start cooking the tomato, which can make it harder to work with -- you effectively want to cook just the bit under the skin, which only takes a few seconds.
I work with a paring knife and a set of spring loaded tongs (but you could use a spider or strainer).
If the skin was still sticking, increase the time for a second or two until you find the right time. If the tomato was getting difficult to hold, decrease the time.
Once you find the right time to cook the tomatoes for, I cook about 3 romas or two larger globe tomatoes at a time -- while one batch is cooling, I peel the previous batch, dip another set, repeat, and you'll have a batch done in no time.
At times, I just cut the skin off. Take a soft fillet knife. Cut the tomato into wedges. Place a slice on the cutting-board with the skin down, with slide the fillet knife against the tomato to cut away the skip, much like you cut away the skin from a fish.
However, this is only practical if you should skin one or two tomatoes. On larger scale I recommend the boiling water trick.
The advantage here is two-fold: peeling is dead easy, and you have as many peeled tomatoes as you need whenever you need them.
The disadvantages are the additional prep-work (which may be significant if you weren't planning on freezing the tomatoes anyway), and that the end result is tomatoes which have been frozen: fine for sauces, not so great for salads.
If you're going to cook the tomatoes after peeling them then I have a very easy method: cut out the tough little core in the top, halve them, and then put them skin side up under a very hot grill for a couple of minutes. The skin rises up off the flesh (some of the skin may blacken, depending how long you leave them), and can easily be plucked off with tongs (or fingers if you're tough).
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