I went ahead and disabled the identifyObsoleteKernels function and here
is the relevant part of /var/log/dist-upgrade/main.log:

2019-06-19 15:37:29,707 DEBUG Obsolete: libisl19 libpoppler85 
linux-headers-5.0.0-13 linux-headers-5.0.0-13-generic 
linux-image-5.0.0-13-generic linux-modules-5.0.0-13-generic 
linux-modules-extra-5.0.0-13-generic
2019-06-19 15:37:29,707 DEBUG Foreign:
2019-06-19 15:37:29,707 DEBUG forced_obsoletes: ['desktop-effects', 
'gnome-app-install', 'policykit-gnome', 'gnome-mount']
2019-06-19 15:37:30,001 DEBUG Unused dependencies: libisl19 pppconfig ifupdown 
libpoppler85 pppoeconf
2019-06-19 15:37:30,001 DEBUG remove_candidates: '{'libisl19', 
'linux-image-5.0.0-13-generic', 'gnome-mount', 'policykit-gnome', 
'desktop-effects', 'linux-modules-5.0.0-13-generic', 'pppconfig', 
'linux-modules-extra-5.0.0-13-generic', 'gnome-app-install', 'libpoppler85', 
'ifupdown', 'linux-headers-5.0.0-13', 'linux-headers-5.0.0-13-generic', 
'pppoeconf'}'
2019-06-19 15:37:30,001 DEBUG Start checking for obsolete pkgs
2019-06-19 15:37:30,100 DEBUG skipping running kernel pkg 
'linux-image-5.0.0-13-generic'
2019-06-19 15:37:30,100 DEBUG 'linux-image-5.0.0-13-generic' scheduled for 
remove but not safe to remove, skipping
2019-06-19 15:37:30,101 DEBUG skipping running kernel pkg 
'linux-modules-5.0.0-13-generic'
2019-06-19 15:37:30,101 DEBUG 'linux-modules-5.0.0-13-generic' scheduled for 
remove but not safe to remove, skipping
2019-06-19 15:37:30,198 DEBUG skipping running kernel pkg 
'linux-modules-extra-5.0.0-13-generic'
2019-06-19 15:37:30,198 DEBUG 'linux-modules-extra-5.0.0-13-generic' scheduled 
for remove but not safe to remove, skipping
2019-06-19 15:37:30,720 DEBUG skipping running kernel pkg 
'linux-headers-5.0.0-13-generic'
2019-06-19 15:37:30,721 DEBUG 'linux-headers-5.0.0-13-generic' scheduled for 
remove but not safe to remove, skipping
2019-06-19 15:37:30,822 DEBUG Finish checking for obsolete pkgs
2019-06-19 15:37:30,861 DEBUG The following packages are marked for removal: 
linux-headers-5.0.0-13 ifupdown linux-headers-5.0.0-13-generic pppoeconf 
libisl19 pppconfig libpoppler85

So just removing the function seems like the best way forward.

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https://bugs.launchpad.net/bugs/1828100

Title:
  KernelRemoval section of DistUpgrade.cfg shouldn't require manual
  updating

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