Most pumps these days have the following types of bolus as a feature.
"A standard bolus is an infusion of insulin pumped completely at the onset of the bolus. It is most similar to an injection. By pumping with a "spike" shape, the expected action is the fastest possible bolus for that type of insulin. The standard bolus is most appropriate when eating high carb low protein low fat meals because it will return blood sugar to normal levels quickly.
An extended bolus is a slow infusion of insulin spread out over time. By pumping with a "square wave" shape, the bolus avoids a high initial dose of insulin that may enter the blood and cause low blood sugar before digestion can facilitate sugar entering the blood. The extended bolus also extends the action of insulin well beyond that of the insulin alone. The extended bolus is appropriate when covering high fat high protein meals such as steak, which will be raising blood sugar for many hours past the onset of the bolus. The extended bolus is also useful for those with slow digestion (such as with gastroparesis or Coeliac disease).
A combination bolus/multiwave bolus is the combination of a standard bolus spike with an extended bolus square wave. This shape provides a large dose of insulin up front, and then also extends the tail of the insulin action. The combination bolus is appropriate for high carb high fat meals such as pizza, pasta with heavy cream sauce, and chocolate cake.
A super bolus is a method of increasing the spike of the standard bolus. Since the action of the bolus insulin in the blood stream will extend for several hours, the basal insulin could be stopped or reduced during this time. This facilitates the "borrowing" of the basal insulin and including it into the bolus spike to deliver the same total insulin with faster action than can be achieved with spike and basal rate together. The super bolus is useful for certain foods (like sugary breakfast cereals) which cause a large post-prandial peak of blood sugar. It attacks the blood sugar peak with the fastest delivery of insulin that can be practically achieved by pumping."
As for type of food...
I personally find that fruit sends my sugar higher chocolate, dark chocolate, cheesecake type desserts.
I choose to do it once a month or so, because if I was to eat it every day I would no doubt crave it more often and end up eating more. My total daily insulin dose would also go up markedly as would my waist line I imagine :)
Also I like to keep my diet, clean and simple as it just makes life easier for me.
I try to keep between 50-100g a day of carbs and keep my insulin needs as low as possible.
I do this mostly to assist with insulin sensitivity, I also believe that insulin can promote fat storage, generally the less insulin I am on per day the better, as Dr Beinstein said "Big inputs make big mistakes; small inputs make small mistakes"
Hope this helps.