How to properly replicate of all distro packages + python packages from an ubuntu server on AWS to an ubuntu server on DO

I’m trying to migrate all the distro and python packages I have on an AWS ubuntu server , to my newly created DO server

Please find below my DO and AWS Distro’s release

• AWS : Ubuntu 14.04.5 LTS
• DO : Ubuntu 16.04.1 LTS

I listed all the distro and python packages I have from my AWS server, with the following commands

sudo dpkg --get-selections > dpkglist.txt
pip freeze > freeze.lst

Then on my DO server, I did the following

dpkg --set-selections < dpkglist.txt
pip install -U -r freeze.lst #to restore the python packages
pip3 install -U -r freeze.lst #to restore the python packages

Yet, there were many errors during this reinstall.

I had to uninstall one package ppp for the dpkg to have everything working properly for the dependances.

For pip , I had to text edit the freeze.lst , manually removing some of the packages to have everything sorted.

The experience was messy, confusing and definitely not clean, IMO.

Questions are the following:

• What should I do to make a clean slate packages , distro and python, import?
• Is there an easy way to do such imports without any hassle e.g with (a) tool(s)?

Thanks