You're looking for REGEX in callflows (only certain users with codes can get through) and this is totally doable in FreeSWITCH, but, again, I don't know if this functionality is exposed within Plivo (although it's feasible for the underlying core, the APIs may not be done yet).
SIP Desktop apps are WAAAAY easier to work with than Handsets, so if they support any kind of registrations, I would imagine desk apps would be supported.
Profig does provide this to businesses in a seamless fashion and eliminates the use of regex etc. They have the capability to support both Desktop and mobile SIP Clients.
Yes, we support automated extensions, and can set them up for you. And yes, we work with SIP desktop apps as well (although our SIP offerings are currently in beta at the moment).
josh2600, do you mind if we handle the support questions ourselves? Thanks! Really appreciate it :)