This problem was fixed upstream but is still present on Jammy (even on 
0.107.1-3ubuntu0.22.04.2).
See 
https://github.com/canonical/netplan/commit/a670781c0f00171d2fb7dd83dbd2de723432a11d


Reproducer:

# cat /etc/netplan/50-cloud-init.yaml
network:
  version: 2
  ethernets:
    enp5s0:
      dhcp4: true


    eth0:
      gateway4: 1.2.3.4
    eth0:
      gateway4: 4.3.2.1
root@jammy-deleteme:~# /usr/libexec/netplan/generate

** (generate:991): WARNING **: 09:33:00.343: `gateway4` has been deprecated, 
use default routes instead.
See the 'Default routes' section of the documentation for more details.
**
ERROR:../src/parse.c:1441:handle_gateway4: assertion failed (scalar(node) == 
npp->current.netdef->gateway4): ("4.3.2.1" == "1.2.3.4")
Bail out! ERROR:../src/parse.c:1441:handle_gateway4: assertion failed 
(scalar(node) == npp->current.netdef->gateway4): ("4.3.2.1" == "1.2.3.4")
Aborted (core dumped)
root@jammy-deleteme:~# netplan get

** (process:993): WARNING **: 09:33:02.396: `gateway4` has been deprecated, use 
default routes instead.
See the 'Default routes' section of the documentation for more details.
**
ERROR:../src/parse.c:1441:handle_gateway4: assertion failed (scalar(node) == 
npp->current.netdef->gateway4): ("4.3.2.1" == "1.2.3.4")
Bail out! ERROR:../src/parse.c:1441:handle_gateway4: assertion failed 
(scalar(node) == npp->current.netdef->gateway4): ("4.3.2.1" == "1.2.3.4")
Aborted (core dumped)

** Also affects: netplan.io (Ubuntu Jammy)
   Importance: Undecided
       Status: New

** Changed in: netplan.io (Ubuntu Jammy)
   Importance: Undecided => Medium

** Changed in: netplan.io (Ubuntu Jammy)
       Status: New => Triaged

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https://bugs.launchpad.net/bugs/2089234

Title:
  /usr/libexec/netplan/generate:ERROR:../src/parse.c:1350:handle_gateway4:
  assertion failed (scalar(node) == npp->current.netdef->gateway4):
  (\"192.168.100.1\" == \"192.168.100.254\")

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