Hi:
For outbound calls, the physical phone port in use isn't relevant. Consider that your OBi has 4 service provider slots, plus OBiBT and OBiTALK, and, as you noted, you can select which SP to use by prefixing the call with a ** command. A phone plugged into either of the two physical phone jacks can use any one of the SPs to place an outbound call.
You can place a second call, while on the first call, using the same, or a different SP, by pressing the flash key. The conference calling function is handled locally on the OBi in this case, vs. on the provider's network, so you can actually set up conference calls between two different SPs.
So, for example, you want to call Jenny in SF using GV, and you want to call Gail in Oxford using Callcentric. First, call Jenny: 415-867-5309. Assuming that you have GV on SP1 set as the default SP for outbound, your call will go out via SP1 (otherwise, you could enter the desired SP to use, e.g. **3). After Jenny answers, press the flash key, then, when you get the dial tone, call Gail: **2 011 44 1865... When Gail answers, press flash again and you have a three-way conference call.