Ok team, I have solved the issue - and along the way learnt a great deal about how PL/CTCSS/DCS/etc tones work.
That said, before I get started I wanted to shout out to @wayoverthere @BoxCar @wrci350 and @Screech for all the suggestions, followups, ideas and collectively all the information that I needed to get this one solved.
With that said, while I now understand it all, and I got it to work, I also realize that while it's easy in my head, it's hard to write down - i'm going to give it a try though so maybe someone stumbles across this one day and it helps them out.
So through my journey I found out a few things:
There are actually two repeaters on the 462.55/467.55 frequency that are relatively close to where I am located - one uses input tone 131.4 no output tone, the second uses input and output tone of 241.8
When i've been testing what has been suggested in this thread, I did have a variable that I hadn't thought to share/I didn't think mattered. I've had the van parked in different spots - and while those spots have been less than 20ft away, that's been the difference between hitting both repeaters clear as day vs barely at all. I've done this several times, it's quite consistent.
So my solution is
Setup two channels, each using their own output tones and both using no input tone.
Set one of the two channels as my secondary channel on the KG1000 - I keep the primary channel on for my simplex comms with my friends
When I receive a transmission I will return transmit on the frequency i've got set as my secondary - if i'm heard, awesome - If i'm not I quickly switch to the other channel and that inevitably gets through without an issue.
What did I learn?
Having no PL/privacy/CTCSS/DCS tone on the receive side means you hear everything on that frequency (I did not know this!)
Line of sight/obstacles do and will have an impact to your transmissions
I'm somewhat lucky that I have two overlapping repeaters that effectively extend my transmission range
Hopefully this explains it all and clarifies the combination of items that happened.
Adam
tl;dr - radio works fine, user needed to better understand radio theory