Probably worth noting that the 'special cabling' for that Nortel system is usually done with standard network cable. Historically CAT-3 would have been used for the phonesets but for many years CAT-5, 5e or 6 has been used since the cost difference was quite small. Most suppliers don't even carry CAT-3 anymore.
So you can go ahead and run wires for the existing system and switch to network phones anytime you want. Usually would just mean removing the wire from the old PBX patch and putting it into the network patch. It never hurts to have a dedicated network connection for voip phones anyway.
Your existing wires may actually be CAT-5. Even 10 years ago they may have used CAT5 for the phones.
You already have some good points on the voip side of things but a bit more on that topic. When comparing hosted vs owned you probably want to look at costs for a 3 to 5 year period at minimum. Further because of your current size you may find that you will grow out of hosted services fairly quickly. Even by Fonality's own site the hosted offering is topping out for 20 users,
http://pbxtra.fonality.com/products/professional/The 'dell' branded stuff looks to be a subset of Fonality's main packages. You might want to look over the main Fonality site if you have not.
As for the DID's, this is probably something that is in favor of working something out with your existing phone company, even if it is to reserve the numbers. Having them attached to the least cost trunk you can get for them might a route to take if they will not actually reserve them without a line/trunk.
If you need something to cost compare for higher ups go price some Cisco or Avaya gear with comparable features. Even a turnkey Fonality system will look inexpensive let alone a DIY TrixBox CE setup.