Here is my upgrade script:

#!/bin/bash

function assert_rc() {
   local rc=$1
   if (($rc != 0)); then
      echo "Aborting on non zero error code: ${rc}!"
      exit $rc
   fi
}

upgrade_options='-o dpkg::progress-fancy=1 -o apt::color=1'

if (( $# == 1 )); then
   upgrade_options="${upgrade_options} -o acquire::http::dl-limit=${1}"
fi

sudo apt-get update
assert_rc $?
aptitude search ~U -F"%c%M %p# %15v# %15V# %d"
sudo apt-get $upgrade_options dist-upgrade
sudo apt-get $upgrade_options autoremove --purge

Hm, the forum totally messes up whitespace in code tags.

In short, to upgrade / update your Debian testing, use this sequence:

sudo apt-get update
sudo apt-get dist-upgrade
sudo apt-get autoremove --purge

Quoting: razing32A bit worried about the recommendation i got during dist upgrade to run "apt autoremove" as there are quite a few packages there.

You need to analyze that list, but it's normally legit. Packages change dependencies, so obsolete ones can to be removed. However don't forget purging configs (apt-get autoremove --purge), otherwise your system will be very cluttered with garbage.

And if suggested remove list looks suspicious (like removing whole KDE or something), then analyze the issue further.

A 32 bit wineprefix shouldn't have "Program Files (x86)" directory, only "Program Files". So something is fishy.
Note, that a prefix is different from the package architecture.

Quoting: ShmerlHere is my upgrade script:

#!/bin/bash

function assert_rc() {
   local rc=$1
   if (($rc != 0)); then
      echo "Aborting on non zero error code: ${rc}!"
      exit $rc
   fi
}

upgrade_options='-o dpkg::progress-fancy=1 -o apt::color=1'

if (( $# == 1 )); then
   upgrade_options="${upgrade_options} -o acquire::http::dl-limit=${1}"
fi

sudo apt-get update
assert_rc $?
aptitude search ~U -F"%c%M %p# %15v# %15V# %d"
sudo apt-get $upgrade_options dist-upgrade
sudo apt-get $upgrade_options autoremove --purge

Nice script :)
I went with the instructions on the debian page for upgrading from stable to testing
Basically replacing the distro name (stretch in my case) with testing and uncommenting the security patches
I then did update , upgrade and dist-upgrade

Quoting: Shmerl

Quoting: razing32A bit worried about the recommendation i got during dist upgrade to run "apt autoremove" as there are quite a few packages there.

You need to analyze that list, but it's normally legit. Packages change dependencies, so obsolete ones can to be removed. However don't forget purging configs (apt-get autoremove --purge), otherwise your system will be very cluttered with garbage.

And if suggested remove list looks suspicious (like removing whole KDE or something), then analyze the issue further.

Will dig into it , but for now , it seems i have wine working fine.
Can take care of the clutter later and do a purge if needed and reisntall the packages if i accidentally remove them.