I'll try to address your questions. If I miss something, please let me know.
David, do you know if what you thought was going to happen with the next release (3.1 is now out) was implemented? Meaning, a person with a single Pro license could install it on as many of the machines they manage from as needed? — Jared Pickerell - DCEduCoop
There have been no licensing changes for version 3.1. The way Pro licensing works, as you've already seen, is that you need to license any endpoint where you need to initiate an unattended session for administration purposes. Remote systems do not require a Pro license. Just install the free version of Connect on any remote systems you need to connect to in unattended fashion.
If you can restrict your admin computer to one computer, you can use it for all your unattended sessions. If you do need to kick off unattended access from another computer, it will need a Pro license.
There are no restrictions on interactive / attended sessions with a remote user / machine. You can use Connect Free for that purpose.
I would "consider" purchasing a $89 a year for my personal use, but would be much more likely if it was less expensive, or if I could make a one-time purchase.
We understand that the Pro pricing may not work for every customer. If you cannot use the free product to serve your family / work, then a Pro subscription would be the next option.
For work use, I could see my Coop paying a yearly $89 for me to use. But I couldn't see them paying $89 for each machine that I use (including home/personal devices), that I may use to use to connect to one of the few RD/Connect machines in the schools and Coop that I remote into. I'd really love my 3 district tech directors and our 1 district tech assistant to also be able to use the unattended access into our management PCs. And what would be fantastic, is to be able to purchase the manged licence to push out the agent to all of our District and Coop PCs and Macs and let any of our tech staff remote into.
Again, you'd just need to restrict starting an unattended session to the Pro licensed computer. None of the other computers require a Pro license. I think this is your understanding, but something you wrote above made me think that maybe you thought all computers need Pro licenses - which is not the case.
Last time i talked to sales [...] If memory serves me right, there were several client settings that couldn't be set in the management console when I had demo'd it (including not being able to set/see/manage the encryption and MFA settings. Maybe this has improved in the last few months
For Managed Connect, 2FA is managed from the login to the management console. You can enable 2FA for all administrator accounts and 2FA will be required when connecting to the management console and allow you to kick off a Connect session. Security credentials are managed automatically in Managed Connect and encryption is always enabled. List price is $34.99 / Month per Admin / Technician if you're a reseller like an MSP. That enables you to access any number of remote endpoints and use any computers to perform unattended administration or initiate interactive sessions with remote users.