Incoming calls land directly to operator's extension (or through an AA)? Which partition do operator and other extensions belong to? What is your "entry" to your CUCM; a SIP trunk?
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You can place the DN of the requested phone to a new (unused) partition. That way, no one will have access to the DN (since that partition will not be present in any Calling Search Space) and the user will be able to place outgoing calls, according to the phones CSS.
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If "term mon" is open, and you simply issue "conf t" and then "exit", do you see anything on the screen? How have you connected to the device?
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If you have used telnet/ssh to login to the device, you need issue "terminal monitor" in privileged more; this command is not needed when you connect through console.
Alternatively you can use "logging buffered" to write debug output to local buffer and later view it with "show logging".
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Can you attach the output of debug ccsip messages and your running configuration? Also, when the call transfer is established, do you see packets increasing at show voip rtp connections detail for the corresponding call? Finally, what is the output of show call active voice brief?
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Normally, adding the CallBack softkey in Ring Out state should have done the job for you. What is you dial out and the destination is On Hook? Do you get the CallBack softkey there?
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How are you connected to the outside? Through a SIP trunk from CME to the ITSP? Can you dial from the inside to the outside successfully? Have you enabled SIP inspection on your ASA?
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The best way would be to use the Bulk Admin Tool (BAT). You practically create an Excel document that contains the MAC/DNs etc, so as to massively create the configuration at CUCM for all 150 IP Phones.
More info here: Cisco Unified Communications Manager Bulk Administration Guide
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This is a DTMF negotiation issue. What is the dtmf-relay configured under your dial-peers (incoming from eg. CUCM and outgoing to Flowroute)?
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Of-course, if MGCP/SCCP integrated, they would be extensions belonging to the same cluster.
If not (i.e. you have an H.323 trunk to the VG), you can always transfer from the IP phones to an "external" number (the analog phones).
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You can create an IVR at CUC using Call Handlers. Also, you can insert you analog phones and extensions (the ones connected at the VG310) in CUCM using MGCP integration.
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