My mom is diabetic so I have a little experience with this. Diabetics are usually encouraged to have stable, limited amounts of carbohydrates combined with fats and proteins at frequent small meals and especially to eat to maintain a healthy weight. You also may want to do some reading on the glycemic index: not all carbs are equal; generally the whiter, sweeter, starchier, less fibrous, or more processed something is, the higher the glycemic index, which is a measure of how quickly the sugars in foods make it to the blood. You would like to have a slower release of sugars to avoid blood sugar spikes, so having meals emphasizing lower glycemic foods is good. Depending how bad the diabetes is and whether insulin is involved, your family member may need to count carbs very carefully and precisely or may be able to just learn some general rules for eating. Usually people with a new diagnosis will have counseling with a diabetes educator who will help instruct on that stuff.
To help reduce "bad" cholesterol, the main advice is to limit dietary saturated and trans fats and increase soluble fiber.
So in practice--this means a lot of meals and snacks centered around vegetables and beans, with moderate amounts of whole grains (especially oatmeal, which lowers cholesterol, and brown rice, which has a lowish glycemic index), lowfat/nonfat dairy, nuts/seeds, lean meats, and fruits. Portion control is important, as is not skipping meals and making sure each meal or snack has a balance of carbs/fats/proteins. A lot of the conventional diabetes diets seem gross to me: lots of fake foods and especially fake sugars, and skimpy little portions. It is possible to follow a diabetic diet using real food in reasonable quantities if you pick carefully, so don't be too put off by lists of meals that consist of things like sugar-free pudding, Butter Buds, margarine, and lowfat hot dogs. It is also possible to use some "fake" things like Splenda and sugar alcohols sparingly to satisfy a strong craving for something that wouldn't otherwise make it into the diet.
Here are some meal ideas--of course there are many more possibilities.
Breakfasts might include:
Oatmeal with milk and/or nuts and moderate amounts of fruit for sweetener
High fiber cold cereal with nuts and skim milk
Whole wheat toast with lowfat cheese
Apples and peanut butter
Lowfat cottage cheese and fruit
Egg whites scrambled with lowfat cheese and vegetables
Lunches could be:
Sardines, rye crackers, and sliced cucumber and carrots
Bean soups with high-fiber crackers
Cold cut or nut butter or hummus and veggie sandwiches on moderate-carb bread with sliced veggies on the side
Salads with some kind of protein
Snacks could be:
Hummus and veggies
Whole grain crackers and nut butter
Handful of trail mix
String cheese and a piece of fruit
Yogurt with fruit
Dinners could be almost anything following your 2/3 veggie, 1/3 protein and starch rule. Beans make a great basis for dinners.
Desserts should be consumed in moderate portions and it's better to have ones with some protein (e.g. frozen yogurt) and/or fiber (e.g. plain fruit, low-sugar fruit crisp with oatmeal-and-olive-oil based topping) than ones that are mostly sugar, white flour, and saturated fat.