For Python2 to Python3 code conversion, Which version of Python & Django best suited?

Currently I am working in big firm where we need to convert python2 old big Django project into python3 version so I have done lots of research related but still not able to find any perfect answer related to which version of Python and Django best suited for conversion.

Currently I am using Python : 2.7.16 & Django : 1.9.13 in my old version.

Anyone can suggest me best suited version of Python & Django for above old version for python2 to python3 conversion.

Solution

I thought I'd add a bit to the strategy advocated by Wim's answer - get the appropriate version of Django working on both 2.7 and 3.x first - and outline some tactics that worked for me.

Python 2.7 is your escape pod, until you pull the trigger on 3.x

your tests should run on both
don't use any 3.x specific features, like f-strings
first Python 3.x, then only later Django 2.x which doesn't run on 2.7
start early, don't over analyze, but avoid the big bang approach
- file by file at first.
- start with the lowest level code, like utility libraries, that you have test suites for.
- if possible, try to gradually merge your changes to the 2.7 production branches and keep your 3.x porting code up to date with prod changes.

Which minor version of Django to start with?

My criteria here is that Django migrations can be fairly involved (and actually require more thinking than 2=>3 work). So I would move to the latest and greatest 1.11 that way you're already providing some value to your 2.7 users. There's probably a good number of pre-2.x compatibility shims on 1.11 and you'll be getting its 2.x deprecation warnings.

Which minor version of Python 3.x to start with?

Best to consider all angles, such as the availability of your 3rd party libs, support from your CI/devops suite and availability on your chosen server OS images. You could always install 3.8 and try a pip install of your requirements.txt by itself, for example.

Leverage git (or whatever scm you use) and virtualenv.

separate requirement.txt files, but...
if you have a file-based, git repo, you can point each venv at the same codeline with a pip install -e <your directory>. that means that, in 2 different terminals you can run 2.7 and 3.x against the same unittest(s).
you could even run 2.7 and 3.x Django servers side-by-side on different ports and point say Firefox and Chrome at them.
commit often (on the porting branch at least) and learn about git bisect.

make use of 2to3

Yes, it will break 2.7 code and Django if you let it. So...

run it in preview mode or against a single file. see what it breaks but also see what it did right.
throttle it to only certain conversions that don't break 2.7 or Django. print x=> print (x) and except(Exception) as e are 2 no-brainers.

This is what my throttled command looked like:

2to3 $tgt -w -f except -f raise -f next -f funcattrs -f print

run it file-by-file until you are really confident.

use sed or awk rather than your editor for bulk conversions.

The advantage is that, as you become more aware of your apps' specifics concerns, you can build a suite of changes that can be run on either 1 file or many files and do most of the work without breaking 2.7 or Django. Apply this after your suitably-throttled 2to3 pass. That leaves you with residual cleanups in your editor and getting your tests to pass.

(optional) start running black on 2.7 code.

black which is a code formatter, uses Python 3 ASTs to run its analysis. It doesn't try to run the code, but it will flag syntax errors that prevent it from getting to the AST stage. You will have to work some pip install global magic to get there though and you have to buy into black's usefulness.

Other people have done it - learn from them.

Listening to #155 Practical steps for moving to Python 3 should give you some ideas of the work. Look at the show links for it. They love to talk up the Instagram(?) move which involved a gradual adjustment of running 2.7 code to 3.x syntax on a common codebase, and on the same git branch, until pull-the-trigger day.

and Instagram Makes a Smooth Move to Python 3 - The New Stack

Conclusion

Your time to Django 1.11 EOL (April 2020) is rather short, so if you have 2+ dev resources to throw at it, I'd consider doing the following in parallel:

DEV#1: start out on a Django 1.11 bump (the theory being that Django 1.11 is probably best positioned as a jump off point to Django 2.x), using 2.7.
DEV#2: get started on Python 3.6/3.7 of your non-Django utility code. Since the code is 2.7 compatible at this point, merge it into #1 as you go.

See how both tasks proceed, assess what the Django related project risk is and what the Python 3 pain looks like. You're already missing the Python 2.7 EOL, but an obsolete web framework is probably more dangerous than legacy Python 2.7, at least for a few months. So I wouldn't wait too long to start migrating off Django 1.9 and your work doing so won't be wasted. As you see the progress, you'll start seeing the project risks better.

Your initial 2to3 progress will be slow, but the tooling and guidance is good enough that you'll quickly pick up speed so don't overthink it before starting to gather experience. The Django side depends on your exposure to breaking changes in the framework which is why I think it's best to start early.

P.S. (controversial/personal opinion) I didn't use six or other canned 2-to-3 bridge libraries much.

It's not because I don't trust it - it's brilliant for 3rd party libs - but rather that I didn't want to add a complex permanent dependency (and I was too lazy to read its doc). I'd been writing 2.7 code in 3.x compatible syntax for a long time so I didn't really feel the need to use them. Your mileage may vary and don't set out on this path if it seems like a lot of work.

Instead, I created a py223.py (57 LOC incl. comments) with this type of content, most of which is concerned with workarounds for deprecations and name changes in the standard library.

try:
    basestring_ = basestring
except (NameError,) as e:
    basestring_ = str

try:
    cmp_ = cmp
except (NameError,) as e:
    # from http://portingguide.readthedocs.io/en/latest/comparisons.html
    def cmp_(x, y):
        """
        Replacement for built-in function cmp that was removed in Python 3
        """
        return (x > y) - (x < y)

Then import from that py223 to work around those specific concerns. Later on I will just ditch the import and move those weird isinstance(x, basestr_) to isinstance(x, str) but I know in advance there is little to worry about.