Repositorry/IM tools/Trisquel 8/frustrations for an average user

Dear all,

Ever since I became convinced of the importance of the Free Software movement, I - an average joe computer user - have been only using free software for my personal computing. I applaud all the efforts.

However, there is much work to be done. Let me briefly explain my situation:
- I have been using Trisquel as my sole distro for some years now, and my use consists of using LibreOffice, browsing the net, and Evolution for email.
- I've become recently interested in using cross-platform communications tools in order to communicate with my parents, and here is where I stumbled with most problems:

* EFF advises using OTR for XMPP communications (e.g. using Pidgin). However, there are known vulnerabilities with OTR 4.0.0, which is the one provided currently with Trisquel 7. So in order to update OTR, I had to compile it from source.
* I am trying to update Pidgin to the latest version, but I am running into a "dependency hell".
* I recently found out about GNU-Ring. Alas, I cannot install GNU-Ring in my computer, which is running a distro that is being used by the FSF, because of another dependency nightmare.
* I was able to run uTox, but when I tried to install better Tox desktop clients, I also ran into the dependency nightmares.
* Oddly enough, I was able to install Signal-Desktop. And that's what frustrates me most: I am able to install Signal, but am unable to run GNU Ring :-(

People might say "but witlh Trisquel 8 a lot of these issues will be fixed", but where is it? When will it a stable version be released? Will be repo be up-to-date, or quickly deprecated? Because of all these difficulties with updating software of everyday use, and unless there is some serious effort (resources) to keep the repo easily updated, I am seriously considering moving to another distro, such as Devuan or straight to Debian (without any of the non-free repos, of course). It is unfortunate that I feel very uncomfortable recommending Trisquel as the go-to distro for an average user.

In an ideal world, what I could hope for is for a few FSF-endorsed free GNU/Linux distros that is easy to install, easy to use, and that is kept up-to-date, so that everybody could be using the same tools in the most secure manner. I think that this will be essential for the spread of free software, but there is a lot to be done until then.

I apologize for being off-topic, but this is a community I cherish and trust.