It sounds like the OP's main purpose is to get from A to B cheaply, and for him taking a roundabout routing is OK. As a general rule, taking a many segment trip is not necessarily cheaper than taking a more direct routing, unless the lowest fare buckets are sold out on more direct routings.

If the OP's departure and arrival cities are fixed, I would recommend starting with Travelocity's flexible date search to find the lowest fares. In almost all cases, the lowest fares from Travelocity's flexible date search or fare listing are the lowest fares offered -- regardless of the number of stops. However, if Travelocity indicates that the lowest fare is sold out for given dates (shows as an 'X' on the calendar display), it is possible there may be availability in the lowest fare bucket on a less-direct routing that Travelocity isn't showing. In this case, you can check the routing rules for the fare (from Expedia) and then use a tool like ITN or ExpertFlyer to see availability for each leg individually. (See the MR Tools sticky thread for more info.)

For example, a recent case for me:

Looking for AA Q fare BOS-DEN (lowest fare found through Travelicity). No Q availability existed for the one-stop routings through ORD, STL or DFW. However, I could fly BOS-ORD-STL-DEN and find Q availabillity.

A travel agent could certainly help with this too.