Got it all sorted out.
Fruitbox running smoothly on a Jessie-based RetroPie image, straight from the EmulationStation main menu.
And I wrote a how-to, so you can too.
https://www.raspberrypi.org/forums/viewtopic.php?f=38&t=188723&start=1594
Thanks much for the input @zerojay , it got me pointed in the right direction!

@mitu alright then, thanks for your help, I'll update my system asap

@mitu Yeah I tried that and it still didn't pickup the controllers

@benret Raspbian Jessie is no longer supported - I think you get a nice message about that when you try to run the RetroPie-Setup script.

Installation on Buster hasn't been 100% vetted, but most bits should work - support for it will probably be part of the RetroPie release that supports the Pi4.

For now, using Raspbian Stretch will give you the best supported Raspbian version for RetroPie.

RetroPie though uses Raspbian Lite underneath, with very little changes added to the system. As far as wireless/networking goes, there's literally no change from a stock Raspbian Lite installation.

I followed this post on how to upgrade from Jessie to Stretch without doing a fresh install and it worked for me. But it's officially recommended to do a clean install.

@dankcushions So... your answer is essentially "Yes, it IS going to be a hideous and massive chore, and yes it IS the only way"?

@Andrewpk200 if you use a crossover cable and hook your pi directly to your pc you can have everything transferred in no time.

Here is another fact, I started a new image from scratch and moved exactly the same amount of roms, the system is duplicated manually in a fresh install and it takes 2.84 seconds more to load ES on the new PI3B+ running Retropie 4.4 than the PI 3B running 3.9, its akward, but true. I have an intro video wich overlays the ES loading screen and now I have to make it that time longer because Retropie 4.4. with a PI3B+ takes more time loading.

My bad, I forgot I needed to disable the splash screen for this to work.

see here

Your log wasnt from RetroPie-Setup 4.3.17 btw but just 4.3 which is some months old.

@raibura hi, did you ever find a solution for this?

Sorry for asking in such an old thread but you are the only person I have found with the same problem as me. Thank you

@herb_fargus I guess he's halfway there then already!

@buzz Awesome, thank you Buzz!

Installed version 4.1 and all seems good so far.

Thanks for looking,
Sam

@BuZz

OSMC support is included

My mistake. I always thought RetrOSMC was installed by some non-traditional means.

As much as I wish that I had an answer for this, I do not. However, I do have resolution. I started over from the bare image again, and rewrote my scripts from scratch to favor ALSA over PulseAudio - and did not install PulseAudio this time around. Considering the other issues that PulseAudio was giving me, in terms of system stability (or the lack of system stability), I can only imagine that my original issues were also related to that.

On the plus side, I've managed to knock together a decent script that gives me what I was after - volume up/down followed by an indicator tone, volume up/down to exit mute state, and a functional mute toggle through tracking the volume and mute states. More complex than what I was trying originally, which was using pactl to control it all, considering that I am on of the "lucky" ones who cannot get ALSA to unmute.

@stahl80 wheezy has been unsupported for months and RetroPie-Setup has been warning this when launched for some time.

@BuZz said in Issues Upgrading Wheezy to Jessie:

You should start from a new RetroPie image (eg v3.8.1) which is based on Jessie (or try the 4.0beta2 image released on the forum here).

Wheezy is no longer supported.

Starting fresh has healed all ailments. Appreciate the advice.