In case anyone comes across something similar in the future or finds this looking for similar...
When a DHCP discover packet is sent it is neither aware of IP OR SubNet
The process takes place over broadcast of 255.255.255.255 meaning anything in my broadcast domain (Which can be used interchangeably for the most part with VLAN, or absence of one as default VLAN)
Think about it, you get your IP/Subnet *from* DHCP.
So you have DORA (Discover, Offer, Request, Acknowledge)
Discover - "Anyone out there to give me an IP?"
Offer - "Sure would you like this one."
Request "Either 'I'll take that one.' or 'I would really like this one instead.'"
Acknowledge - "Alright, I have you marked as having that one proceed.'
With that exchange comes an IP AND subnet, and if any host lives in the broadcast domain on a higher subnet, you just made orphans...
Subnets overlapping is almost always a bad idea because it can lead to this and other confusions, thus unpredictable behaviors. If you are sub-netting for a reason, it is assumed to be logical isolation, and you should be routing between them.
Otherwise, you have IPs that can send to other IP endpoints that have no way to respond, for which I can think of no valid reason.