1) Each item in RMS can have 4 prices associated (Regular Price, Price Levels A, B and C). There are several types of discounts that can be applied to items, including quantity discounts. An Item can also have a 'Sale Price'. Sale Price and discounts can be activated based on a schedule - so you can set a sale to expire on a certain date. Customers can be associated with a price level or given a flat percent off discount (Levels are a much smarter choice).
2) RMS does include work orders with the ability to deliver multiple line items at different times. RMS also inculdes an item type called "non-inventory" which is commonly used for Labor Items...
RMS at least addresses the areas that have enqured about, but you should work with a reseller to go over your detailed requirements.
There are third party add-ins to RMS that extend both of these areas if the built in features don't meet your needs.
Good Luck!