Perform all tests with the Homeseer device connected directly to the OBi via a telephone cord to the OBi's RJ-11 jack. Do not test via the home's wiring.
The fact that you hear a dialtone on the OBi after the Homeseer dials means that the OBi isn't getting a sufficiently high enough audio level of DTMF from the Homeseer, or conversely, the signal is too high, and/or the signal is distorted, such that the OBi can't recognize the DTMF. This is probably the Homeseer's fault.
Why don't you contact them for support? Perhaps the gizmo has some settings in that regard.
You can experiment with the ChannelRxGain setting, both up and down, to see if you can find a "sweet spot". This setting controls the amplifier gain on the OBi, when it is receiving a signal from the telephone, or in this case, from the Homeseer dialer.
Remove both check marks to the right of any setting to be able to edit that setting.
Do NOT listen into the audio from a telephone on a splitter. That is significantly altering the impedance and gain of the signal.