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I have a "server" that's always on in my house (It's an old desktop, but it runs Ubuntu Server and acts as a fileserver). I installed a VM for FreePBX and purchased a Cheap-ish IP Phone and set that up as my "business" phone, with a free Google Voice number. All business calls are directed to that phone number, and it works for me.
If you don't have a always-on PC around your house you can run a VM on, I've also heard good things about running FreePBX on a Raspberry Pi, which is like $35 for the board and you would need to get an SD card and an ethernet cable.
But, basically, sub-$100 free number business phone that is right at your desk. Cheaper than buying a cell phone, and more businessy.
I worked in the music business for years, so I always just had friends compose stuff for me.
FreePBX has this in their forum links: http://www.freepbx.org/support/documentation/howtos/where-to-get-free-classical-music-on-hold
It will probably need additional compression, which you can do with ProTools/Audition/Audacity.
Basic compression tutorial: http://www.soundonsound.com/sos/sep09/articles/compressionmadeeasy.htm
Asterisk is what you're looking for. Super powerful. However, if you're just looking for a quick way to get into a small system at home, FreePBX will do the trick. It's Asterisk based and has a nice web panel.
Just download, burn, and install on an available machine. You can even hook up with SIPStation for an easy phone service. http://www.freepbx.org/
Buy or repurpose any old server and install the Free PBX distro. All-in-one package will take care of your software install.
http://www.freepbx.org/download-freepbx
There are a ton of guides out there for setting Asterisk/FreePBX up if you have any trouble. Feel free to shoot a PM as well if you give it a shot.
After that's set up you'll need IP phones if you don't already have them. I've got 100+ Grandstream phones in use and haven't had any issues to speak of. I purchase mine from thetelecomspot.com. You can get their mid grade models for ~$70.
You'll need a SIP service provider and I've used nexVortex for years and would highly recommend them.
Other than that all you need is a reliable internet connection.
The combination of FreePBX and pfSense can do everything you need. FreePBX is an open source PBX for SIP which will allow you to manage and deploy several phones or softphones with all the features you require.
pfSense is an open source router device that will allow you to manage VPN's and have finer grained control over your internet connection. It can also be used to create a VPN between your home and your parents which will simplify the encryption side of things for the call.
First, asterisk <> freepbx
With any of the GUIs, you have many additional security vulnerabilities. FreePBX gets a decent, critical vulnerability at least once a year. This one was really nasty.
That being said, there are many ways that your system can be compromised...
a) Local virus. There are local hacks on a system (click bait, etc.) that then scour the local network for voip servers and launch the attack internally.
b) Phone attack. Whether from virus, voicemail, or others, phones are also vulnerable. A good yealink attack happened last year that used a redirect to get the international calls.
those are two examples of a system that can be hacked that's not even connected to the internet.
Like /u/BaconX2 said... more info is needed about how these calls originated to determine where they gained access.
Also...
> The box isn't update with the latest updates and security patches because that generally breaks PBX In A Flash
That's a horrible philosophy and perhaps if that system isn't working for you, then you need to consider a different one... such as Asterisk (without the gui) or if you need the GUI, a new install of PBX in a flash or FreePBX.
There are many serious vulnerabilities out there. Not updating your system can be a very expensive mistake.
The FreePBX distro (http://www.freepbx.org/freepbx-distro) is the most stable, up to date, and supported version of Asterisk with a web gui that is Free.
If you are willing to spend money on it, consider trying Switchvox (http://www.digium.com/en/products/business-phone-systems).
If you are wanting to just use Asterisk to accomplish a specific goal (more so than just a PBX) or don't mind learning and configuing all the features yourself so that you have total control over the situation - use just Asterisk itself. There is lots of online documentation on how to do things, but start with the Definitive Guide (http://it-ebooks.info/book/2332/).
BTW, trixbox is no longer a current or supported distro, and AsteriskNow is a perfectly acceptable option in place of the FreePBX distro as it is nearly the same.
I would say to try different aspects of "IT" and find out what you enjoy and what you hate. Learn a little programming, build an operating system from scratch, put a few PCs together, learn about VoIP. Just don't think you have to have your entire future decided in the next four years.
FreePBX is a ready-rolled system that is simple* enough. Otherwise, take a look at Google Voice (if you're in the US) and there's bound to be a myriad of leased "cloud" (I hate that word) mini-PBX providers available wherever you are.
* Amongst other things, I am a phone/VoIP tech.
It's not clear exactly what you're looking for. Paid support is available from Sangoma:
http://www.freepbx.org/support-and-professional-services
For free support, the FreePBX forum will probably answer all your questions:
For most phones, I like AAstra (Mitel now) 6730 series. They're built like tanks, easy to configure, and have good speakerphones. And the 6739 is a pretty sweet phone- as long as you don't mind paying $300+ for it, you get a big color touchscreen and Bluetooth built in. I personally haven't tried the 6800 series because I don't like the interlaced softkeys...
For conference phones we run the Polycom SoundPoint IP 7000. Not cheap but it sounds bloody amazing.
I also like Snom 300 series for a hobbyist perspective. They're very tweakable and they can load custom ringtones on the fly.
The newer Grandstream's aren't bad, but I'm not a fan of the Android ones because there are tons of settings you can only change from the LCD panel.
Yealinks I've heard good things but never actually used one.
Finally, for a platform try FreePBX
//edit: Why the downvotes? Is it because I suggested another vendor (which has since been removed)?
Check out FreePBX
I currently have it running on a simple PC and a SIP service from voip.ms. You can use either SIP phones or get an ATA device that will let you connect your current phones.
At your price point, look at FreePBX as a phone server and FlowRoute as a SIP service provider. Since FreePBX is built on Asterisk you should have all the future flexibility that you need.
Regarding PRI vs SIP, just prior to coming on-board at my current employer they installed PRI over Fiber at each office which essentially is just SIP converted to PRI. Many service providers are going this route and all it does is add an additional layer of failure into a system. Going SIP also allows for tons of additional flexibility down the road.
I really wish I remember exactly how I set it up. Basically, I installed a VM with FreePBX http://www.freepbx.org/ and then within Asterisk they have a page for Google Voice stuff. Here's the guide I loosely followed when I installed everything.
I can't remember if I put my VM on the RAID or if I left it on the filesystem, so if I have to rebuild it I'll take better notes and then write up a guide or something like that!
Thanks! That suggestion uncovered more of what's causing the issue. Now to try and digest these error messages.
It's running a 1.6 of Asterisk, which has already reached EOL. I wouldn't recommend it. The current versions are Asterisk 1.8, which is the long-term, and Asterisk 10. Check out the FreeBPX Distro http://www.freepbx.org/download-freepbx. You can even go with Elastix if you want Asterisk + extra stuff like Jabber and Mail.
Documentation: The Asterisk Book (in HTML): http://www.asteriskdocs.org/en/3rd_Edition/asterisk-book-html/asterisk-book.html. You can also buy it here.
I had no idea Trixbox was still around. You might try PBX in a Flash or FreePBX if you need an easy-to-setup Asterisk + GUI. I always just do everything manually with text files, so it has been a while since I tried out any of the GUIs, but the aforementioned two seem to be some of the most popular.