The actual ssh process is not complicated. If done as you want, you just create an account in the EC2 machine, and keep an ssh open with autossh from the work machine to the EC2 machine. Others have already pointed out the article you need, start autossh reverse tunnel automatically when network comes up
There are several disadvantages of diverting the traffic through the EC2 server. One of them is that you actually pay for usage and traffic in AWS, other is the slowness of using ssh connections tunnelled inside ssh connections, another is that it will be not impossible but cumbersome to tunnel UDP connections on top of the TCP ssh connections, and lastly the longer RTT involved in the packets travelling to the nearest AWS center and coming back.
You can also have legal issues into data or traffic from projects you are working leaving the national borders.
Another alternative is setting up in the home router a machine in the DMZ area, and for instance, accessing a www site in the EC2 machine that is visited every say 5 minutes by the work machine, the work machine will establish a connection to your IP address. (more in that later)
I also would prefer using IPsec or OpenVPN than ssh. I have had ssh for a while, and the process of having to correctly setup tunnels to access different services is tedious and cumbersome.
As for the IP address of your home machine. You do not need a static one, you have services like FreeDNS that give you a DNS entry that maps to the dynamic IP address the ISP gives you.
I have done actually here a different thing. I placed the ISP cable modem/router combo in bridge mode, and connected there a Raspberry PI compatible/Lamobo R1 with an wifi chipset, 5 ethernet gigabit interfaces, and a SATA port + SSD disk running Linux.
If you notice, this is a very interesting machine with a low power requirement.
I connect to home using an IPsec VPN based in StrongSwan to my dynamic IP address using a DNS name provided by FreeDNS.
The VPN is configured in such a way, that the native IPsec clients of my Macbook Pro and iPhone are able to connect to the VPN without installing any free additional software.
Once inside the VPN, and only inside the VPN (and at home) I have:
- access to ssh,
HTML 5 videos,
Voip services via asterisk w/ a trunk to my phone operator to allow me to make calls to any local operator that I use when abroad,
BIND with RPZ,
hostapd to give wifi to home.
I also have a switch chipset in that box, that separates two VLANs, the outside connection and the internal network.
In the rest of the ethernet ports, I connected my Smart TV and my Apple TV, so I can stream from any point at home to them.
My work machine is also configured to keep a permanent IPsec tunnel open to this home router, so I can log in anytime in it.
Link about permanent tunnel with StrongSwan: