I have found that trying new recipes gives me better results than trying to make my old favorites, with few exceptions, because they usually don't come out quite the same and I'm always comparing it to the original. A lot of people say you can just cut the sugar in half in most recipes. I have not found this to be the case. Sugar acts as a liquid in recipes, but it also crisps things up and caramelizes nicely. If you just add extra water, it just tastes watered-down. Sugars are often put in to compensate for a lower amount of fats, so if you are ok with that, you can just add more of a good quality fat (including dairy). We are a bunch of skinnies in our house, so we don't mind at all doing that, but I know most people would rather have the sugar than the fat. I personally am convinced that good fat doesn't make you fat, but that is another topic.
Honey is our go to substitute. If you can get your hands on a very light flavored, raw, unfiltered honey, you are set. If it has some bitterness, it may come through in the flavors.
Maple syrup (not the maple flavored corn syrup, of course) is our next choice, simply because it costs more and we can't get it locally produced. Something where the flavor of honey would compete rather than compliment can often fare well with maple syrup. Dairy based items seem to be complimented better with maple, like ice cream, or steamed milk. Chocolate blends well with maple (though a darker chocolate flavor can get by with a good honey). Both honey and maple syrup are sweeter, but I don't usually reduce much if I am serving it to my husband or anyone outside of my family.
Fruit is of course our preferred sweetener, though it isn't as versatile. This is more for practical additions, like to sweeten your morning oatmeal. Whole recipe books have been written using fruit juice concentrates. Vanilla and cinnamon both give the illusion of additional sweetness without adding extra sugar. Sometime I will throw nutmeg in waffles and muffins and that gives it the depth of flavor so you don't miss the sugar. Salt or roasted nuts can give the same effect. And, of course, we mentioned fats--coconut oil in particular gives a luscious, rich tone.
There are a lot of health food sugars like coconut sugar, agave, sucanut, rapidura, and stevia but as you may have noticed, I like to stick to things I can get at a grocery store or from my local farmer. I see these special sweeteners more and more often in my grocery store, but they just aren't as reliably available to everyone. Plus, it's cool to use something made by people I know (or could know) without a factory!
As I bake, I taste and smell everything. If it tastes good raw, it will likely taste good baked. If it has eggs, you can taste before putting in the eggs.
Let's looks at specific desserts. Drinks are some of the best treats to sugarfree. Juice concentrates, particularly white grape juice, can easily be added in a slightly higher amount than the sugar. Fruits in blended drinks and frozen mixtures works very well, and anything with an already fruity flavor is usually even better with a stunning specimen of the real thing. Icy desserts use the same principles. Hot chocolate and steamed milk are best with maple syrup.
Muffins, pancakes, and other quick breads are great with a direct honey substitution or added fruit, vanilla, and cinnamon. These especially benefit from coconut oil. It is expensive, and seems to yield the greatest use per price when applied to the outside, rather than baked in, though if you can afford it, it is awesome inside. What I mean is that I sometimes brush coconut oil on the loaf pan or waffle make instead of a spray oil.
Pies are an awesome sugarfree dessert. Baked fruit pies can be all fruit or with honey. Cold pies can use a gelatin base and get their sweetness from their own fruit. Pies like pecan pie I have not been able to master, as the crispiness does not come from an alternative.
Cakes with a texture of muffins, such as a coffee cake, will do great with honey. If they have a lot of eggs, they are light. In general, cakes are not the best to make over. I usually try something already out there. Cookies are similar. If they have a muffin texture they will do well. A crispy cookie won't come out of honey. But, of course, you can still have your cake and eat it too. A rapidura or raw, organic sugar are a better alternative in cakes and cookies than totally processed sugar, and can often be used in smaller amounts, though of course the flavor with be more molasses-y. When we were transitioning, just a touch of one of these seemed to make the recipe just right. Unsweetened carob chips are pretty good, and if you can find a cookie you like, but not a good chocolate, there is a far smaller amount of sugar in a few chips rather than the whole cookie. We usually put golden raisins and nuts instead of chocolate chips. A cream cheese honey frosting can do wonders for a cake and you can put a little on your kids' and a lot of your husband's!
Granola and granola bars are usually perfect to substitute for honey. If you are going for a crispy granola, it will need enough fat to do that rather than the sugar.
Fruit puddings, lemon flavored desserts, and jelly consistencies are too light in flavor for most honeys and maple syrups and usually do well with white grape juice concentrate or other fruit base--of course use a greater amount and reduce the liquid accordingly. Dairy-based pudding and rice pudding do well with maple syrup.
Hopefully that gives you a good overview to dare venture into your own world of sugarfree. If you find something you love, please pass it along! I am alway looking for new ideas!