Comment 2 for bug 1808773

Yes, unfortunately it is still a problem.
There was an update to libssl available today (libssl1.1:amd64) but also after this upgrade I get the same error:

Installing from repository:
$ sudo apt install python-boto
Reading package lists... Done
Building dependency tree
Reading state information... Done
Some packages could not be installed. This may mean that you have
requested an impossible situation or if you are using the unstable
distribution that some required packages have not yet been created
or been moved out of Incoming.
The following information may help to resolve the situation:

The following packages have unmet dependencies:
 python-boto : Depends: python-requests but it is not going to be installed
               Depends: python:any (< 2.8)
               Depends: python:any (>= 2.7.5-5~)
               Depends: python-six but it is not going to be installed
E: Unable to correct problems, you have held broken packages.

Installing with deb-package:
$ sudo dpkg -i python-boto_2.44.0-1ubuntu2_all.deb
Selecting previously unselected package python-boto.
(Reading database ... 190250 files and directories currently installed.)
Preparing to unpack python-boto_2.44.0-1ubuntu2_all.deb ...
Unpacking python-boto (2.44.0-1ubuntu2) ...
dpkg: dependency problems prevent configuration of python-boto:
 libssl1.1:amd64 (1.1.1a-2+ubuntu18.04.1+deb.sury.org+1) breaks python-boto (<< 2.44.0-1.1) and is installed.
  Version of python-boto to be configured is 2.44.0-1ubuntu2.

dpkg: error processing package python-boto (--install):
 dependency problems - leaving unconfigured
Errors were encountered while processing:
 python-boto