I too was an Hyperspin user. These days i can't stand the slow bloated shitpile.
AttractMode is very easy to use, it's just when you get to themes/plugins etc, that it helps to be familiar with at least one or two programming languages.
Great excuse to learn, if you aren't a programmer of some sort already.
1: There was somebody working on a layout editor, from I understand, they threw in the towel.
I've considered writing one myself, I dunno.
2: This could be done with script by checking the [title] and executing another layout script.
3: I'm using Hyperlaunch with AM for the moment. But also, you can do this in scripts.
Specifically the transitions Transition.FromGame and Transition.ToGame, combine those with being able to have a separate layout for each emulator, and you shouldn't have a problem.
For example, Transition.ToGame could run fe.do_nut("mame.nut"); which would be a script that executes xpadder.exe and sets a profile.
AttractMode is extremely powerful once you start digging in to it. It's just not point and click, and requires a functioning brain with the ability to learn.
Have a look through the extras on github.
Also, I've written my own layout, feel free to have a look
https://github.com/Luke-Nukem/attract-extra/tree/master/layouts/swapper