It sounds like your biggest issues are OSX-related, perhaps even your 
desire for ease of use features like GUI settings.

And I realize it's not a good answer, but note that I use virtual machines 
for a few legacy apps that don't run on my current platform, and in fact 
some are set up to auto-launch so they're always-available. Takes a decent 
amount of RAM (cheap these days) and a little up-front work to get going, 
but after that it's just like launching another app.

Also my understanding is that the way Leo is coded means that a given 
"recent release" isn't in any way more stable than the nightly snapshot - 
perhaps I should phrase that - the nightly snapshots are just as stable as 
the release (99.x% of the time); it may even be true that the posted 
release doesn't get any extra testing at all other than by new users, and 
are just posted to comply with the usual convention for those not familiar 
with Leo.

In fact at this point the release is more of a "legacy" version, as it 
always will be once a few weeks goes by without it being updated.

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