1. I would replace the 10/100 NIC in the 2600 system with an NC360T. As for the Killer NIC I would keep that until you have any issues with it. No need to replace something that is not faulty.
2. I think what you are talking about here is what is shown in the video (NIC Teaming). Whilst this is possible the process is incredibly difficult and I'm not even sure if it is supported in FreeNAS or any Windows version past 8. In addition, unless you have an SSD or a very good RAID 100 or 5 array you will be bottlenecked by the speed of your storage drive (E.g. If the max write speed of the drive you are accessing is 100mbits the max speed you will be able to access your files would be 100Mbits, even if you used 1gbit ethernet) If you did want to increase transfer speeds and the PCs were not too far apart you might want to invest in an SFP card (Example) and SFP cable. This is a lesser known standard based off SFP fibre cable that deliver 10Gbit networking speeds (For more info see this video) Would only recommend it though if you have an SSD as it is way overpowered for a HDD.
3. While it is not necessary to upgrade the switch you might want to think about upgrading anyway. The port based QoS is probably going to be a bottleneck. Would recommend a Netgear ProSafe 8-port as a replacement. I have one and they are very durable and very easy to set up.
4. No. Although I have personally not used the Comcast Gateway, this would cause most routers to have DHCP clashes as it would see all the devices connected to the switch twice. Also unless you have internet that is faster than 1Gbits there is no benefit to you.
As for your additional comment about SMB at the bottom. SMB is a type of netowrk protocol that allows you to share files and access other PCs acrosss a network. it includes a variety of useful tools including permissions (So you can limit certain peoples access to documents) and connection are digitally signed so you know who they are coming from. SMB is built into every Windows version and is very easy to use and can be used on Linux and Mac OS X with a bit of config.
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