Property Listings Website: Mashup vs Ubercart

I am building a real estate website which needs to email property inquires to agents.

Requirements:
-Users want to inquire about several properties at once, so a cart or flagged list is needed.
-Only one of the agents on the list of inquired properties should be emailed (A property has only one agent).

Workflow:
-User adds several listings to their list.
-User provides contact details and submits the list
-An agent from one of the properties is emailed (to save a customer from dealing with multiple agents).

Since this workflow is very much like a shopping cart I thought of using ubercart (6.x) for this. Users would add listings to the "cart", go through the checkout entering some contact details then conditional actions (an ubercart feature) would email the "order" to the agent belonging to the first listing in the cart. All the keywords would renamed to suit the audience, e.g. inquiry instead of order.

A friend suggested I go with Views, CCK, Flag, Token, Actions and Triggers modules to make a mash up, this would supposedly be more flexible and future proof.

Ubercart has the most functionality out of the box but may be overkill for a this.

I would like to know the advantages and possible pitfalls of both options.

Thanks.