Without changing any settings, have a look in OBi Expert Configuration at the following:
Physical Interfaces > Phone Port > DigitMap:
([1-9]x?*(Mpli)|[1-9]S9|[1-9][0-9]S9|911|**0|***|#|**1(Msp1)|**2(Msp2)|**8(Mli)|**9(Mpp)|(Mpli))
Physical Interfaces > Phone Port > OutboundCallRoute:
{([1-9]x?*(Mpli)):pp},{(<#:>|911):li},{**0:aa},{***:aa2},{(<**1:>(Msp1)):sp1},{(<**2:>(Msp2)):sp2},{(<**8:>(Mli)):li},{(<**9:>(Mpp)):pp},{(Mpli):pli}
In the two places that # occurs, does it look like the above?
Also can you post what this is set to:
Physical Interfaces -> PHONE Port -> PrimaryLine : ?
One more test – if you dial **8 followed by a number, does it go out via Ooma?