I am serving dollar roll sandwiches with 3 kinds of meat. I wasn't sure if your 5 sandwiches per pound was for dollar sandwiches or bigger.... I will be preparing the sandwiches with (the layer of butter of course) meat & cheese ahead of time to help control my portions. How many pounds of each (shaved) should I buy?
Turkey
Ham
Roast Beef

Along side I am only serving a vegetarian pasta salad and then 3 varieties of desserts. I figured a nice good serving size on the pasta (1/2 - 3/4C per person) and 2 desserts per person.

I think I'll only serve lettuce, pickles and possibly tomatoes on the side with Dijon Mustard, Horseradish Mayo (for the roast beef) and Regular Mayo. But how many heads of lettuce, pickles and tomatoes will I need?

If you are responsible for setting up serving and cleaning up, you need at least 10 people (at $100 or more per person) to serve this large a crowd.

In most states it is illegal for you to serve food for sale unless it is prepared in a licensed kitchen or the kitchen of the host.

Also, you need event insurance, as you are legally liable for any sickness or injury to guests or staff, even if it is "not your fault". You need event insurance; you can be sued (lose your house, etc.) if someone is injured cooking or serving or eating the food.

In addition, this is much too light a menu for this event, especially for 4 hours. At a minimum, I would add an appetizer table, plus two to three other dishes.

See this discussion- I sent this new caterer to this pro board, and you could post there too;

www.cheftalk.com/forum/thread/66326/low-budget-wedding-for-175

And please also read these two threads:
www.ellenskitchen.com/forum/messages/27018.html

For dollar sandwiches, only 1 1/2 ounces of meat, so a pound makes about 10. Women tend to eat 2, men 3, and I add 10% for extra. So an example of the estimate would be 100 women= 200 plus 100 men=300 total 500 plus 10%=550. At 10 per pound, 55 pounds. With these three meats, I would do 30 pounds (300 sandwiches) beef, and split the rest between the other 2.

What I would NOT do, is add the cheese. Instead, I would allow 1 ounce per sandwich (550 sandwiches =34 pounds, cut in 1 ounce squares that would fit the buns, and served on trays. This will fill the tables better, it look like more. It acts as an appetizer type tray. It allows people choice of cheese (Swiss, mild cheddar and jack at a minimum) and allows the many people who don't eat cheese on their sandwiches to do avoid it (otherwise you will likely find yourself throwing away cheese that has been removed).

I would also do at least 1 tray of peanut butter and jam, unless there are no kids in the party.

Condiments needed for 100 people are about the same regardless of the size of the sandwiches, see the condiment table on the sandwich page for amounts.

1 pound shaved or pulled makes 12 sliders, enough for 5 people. For each dozen, I would plan 5 pulled, 4 ham and 3 turkey if the party is not dressy, or 5 turkey, 4 pulled and 3 ham if it is- the drip factor.

Put out a platter of quartered cheese slices next to it, 1/2 ounce (2 squares) per person.

Do 3 classic relish trays, see the veggie tray page. Squirt bottles of regular and spicy mustard.

1 pound chips per 12- 15, 1 pint dip or salsa per pound

If there is alcohol served, plan dinner level coffee with the sandwiches, see the beverage planning page.

If these are standard 1 pound loaves, the recipe you give would be about 20 people.

If people make their own, add 10% more of each. 1 tablespoon mayo, put mustard on the side. Have a dozen cheese only for any non-meat eaters.

You can go to 8 per pound meat and 12 per pound cheese, t his is a smaller sandwich.

www.ellenskitchen.com/bigpots/plan/quan100.html