I was checking out your app and played around with it and this happened...
 
 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I feel like this version of Descent is going to push a lot of people to say “you know, I’ve been wanting a game like this for awhile, maybe it’s time to see what all of the Gloomhaven hype is about...”
 
 

16 quests. $175. Sorry, this is a hard pass. Gloomhaven Jaws of the Lion is 25 scenarios for $50. Miniatures are cool and all but... yikes that’s a big ask for what is basically a third attempt to make Descent relevant. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

I hate to start a new forum for a new game with a negative, but this is going to be a hard pass for me, at least for the time being.  They didn’t even finish 2E.  I’m also not a fan of the artwork, and the characters aren’t even the same. 
 
i don’t know. I’m sure someone is excited about this, but at that price tag I’m just wishing more of those resources would have been put into 2E. 

First of all, nice note-taking skills.  It's helpful for newer players to have a breakdown like this.
I just noticed one problem with what's in your notes: I'm not sure where you got the idea that Free-triggers will provoke an AoO.  The only thing that provokes an AoO is an action, and only if that action isn't a Fight, Evade, Parley, or Resign.
To answer your question, yes you can cumulatively use a free-trigger in the way you described.  So long as you continue paying the 1 resource for Physical Training, you will continue getting a +1 bonus to the chosen skill for that particular skill test.  The section you are looking for is under Modifiers in the rules reference: