Is this worth using or not?

We are just looking into using outlook integration and have one sales guy trialing it. He is already frustrated with the options but since this is a new tool, perhaps others know the ins and outs better and can provide some valuable insight, warnings, workarounds, etc.

First some basics:
1. Leads always are set up as "Individuals". Only when they reach the Prospect stage do they become "Company" records.
2. In our general preferences we do NOT have the 'Show Individuals as Contacts' checkbox checked.
3. Sales people want to be able to sync their contact list with contact records, however they also want to be able to identify some of these contacts as leads and sync email messages with the "Lead" record rather than the "Contact" record.