Understand structure of Chrome User Profile data to Transfer to new PC/ OS & avoid Settings corruption Error?

Older answers are not working so I'm including things that may work in pieces.
Chrome Version: 44.0.2403.155 m - 44.0.2403.157 m

I used to be able to copy entire Chrome User Profile\Default from OS to OS and PC to PC.

C:\Users\\AppData\Local\Google\Chrome\User Data\Default

Chrome 44 Stable is more strict. I updated Chrome on both Win 8.1 instances (actual clones) to latest stable Chrome release. I did a copy + overwrite of Default "User profile"& it fails to work.

The resolution/ answer lies in figuring out the structure of User Profile data (folders & files) & what parts of it should be left behind v/s which ones to be migrated.

This error occurs due to changes in Chrome but weirdly, it does not occur on the source PC/OS.

http://www.ghacks.net/2014/04/18/google-chrome-changing-browser-settings-automatically/

Chrome detected that some of your settings were corrupted by another program and reset them to their original defaults.
| Learn more | Reset all settings | Sign in

Quote from Learn more:

Settings that Chrome protects from being changed
Default search engine
Homepage
Startup pages
Pinned tabs
Extensions
If Chrome resets your settings and you’re not signed in to Chrome, your settings will be reset to their defaults. If you’re signed in to Chrome, you’ll still see your customized settings.
Sometimes programs will keep trying to change your settings. If this is the case, Chrome will continue to reset your browser settings every time it launches. You'll always be able to see your customized settings by signing into Chrome.

Apparently, as per this thread here, recent versions of Chrome (but not Chromium) seem to be doing some extra 'unwarranted protection' and reset everything without asking the user.

Is it possible to find out what part of settings (files, folders) are causing this error?

To ignore those parts and/ or
Select parts of User Profile data that will migrate without error?

Thing's I'd like to transfer migrate for sure:

Bookmarks (I think this syncs via Google Profile)
History (No idea what syncs - I use months & years of history to traceback and recall things)
Passwords (partially syncs via Google Profile)
Cookies (Not synced) (Important for forums I frequent)
Extensions (synced but No Data or Settings synced)
- Extension Configs/ Settings + Extension Local Stored Data (Very important)
- (Especially, in extensions like Session Buddy I have stored stuff for few years now)

(Some of this is easily synced via Google account but all of it does not pass over)

Some individual, but older information on transferring/ copying specific items:

Extensions:

..\AppData\Google\Chrome\User Data\Default\Extensions

https://productforums.google.com/forum/#!topic/chrome/6EVtjeaWObs
https://stackoverflow.com/questions/14543896/where-does-chrome-store-extensions
Where does Google Chrome save LocalStorage from Extensions?
https://superuser.com/a/473770/183467 - Re-Packaging as .crx: For a more compact version of your extensions (rather than the unpacked, folder version), you can use Chrome to re-package them into .crx files. I use this when I notice I still have an extension that is no longer available on the Chrome Web Store, and therefore will not sync back.

Cookies:

C:\Users\Your User Name\AppData\Local\Google\Chrome\User Data\Default\Local Storage
%localappdata%\Google\Chrome\User Data\Default\Cookies
chrome://chrome/settings/cookies

Some examples of this not working or people facing issues here:

Some Outdated methods:I found some relevant methods, articles & answers which I have used before. I believe they are outdated now, given that Chrome has changed how it works with/ locks down User Profiles.

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