I gave it another shot with Jessie and figured out a way.Instead of using isc-dhcp-server and tftpd-hpa I tried out dnsmasq. I’ve used it in the past and honestly forgot about it. Works like a treat. I ran into another issue but that was my mistake. Jessie doesn’t come with a proper version of syslinux for older BIOS type systems so with out really thinking about it I mismatched files from different versions and this caused it to break. I removed the mismatched files and downloaded syslinux 5.10 and now I can properly PXE boot a system image.
I still don’t know why but idc-dhcp-server and tftp-hpa were fighting each other. Could be just a broken binary and I didn’t try to compile from source.