From major version to major version directly or with stops

[Mac2013orlater]

Actually I enjoyed Apple offer (strategy) for upgrades of o.s. if the from-version and to-version are not adjacent versions. Direct upgrade supported (even recommended) and only that possible if installers for intermediate versions are not available - this way seemed for me to be less costly as with stops on intermediate stations.
Addressed are here upgrades of major versions, e.g. El Capitan to Sierra.
In case here it was from Mavericks to Sierra.

Having the upgrade completed, fresh after completion I am no more sure if it was the optimal journey flow as Apple stock apps like to change formats of data handled and stored by them on change of o.s. major version increase. The longer distance between from-version and to-version on o.s. upgrade the more data format changes might had happen on this distance. It is always easier to make single conversion than to chain such conversions. Risk of errors is higher on chaining format conversions.
So with my upgrade 10.9 to 10.12 I experienced several problems regarding Apple stock apps - some are addressed here on MacRumors forum.

I wonder if the outcome would been better if I had make journey from Mavericks to Sierra with stops on every (or some) intermediate station(s). Anybody likes to share own opinion? Your input is welcome.

P.S. However this was only option for me as I missed the opportunity to download Yosemite or/and Capitan installers. Got informed those days it was not possible to break the process between installer download completion and o.s. install/upgrade process but no plan had compiled how to handle all my backups on upgrade. My fault to not had invested time into matters of installers availability. Got informed also those days direct upgrade to distant major version was not supported.

 

[Ebenezum]

I am not certain I understand your question.

In principle upgrading OS one version at the time offers no benefits assuming Apples software can recognize previous data formats without any problems. On the other hand there have been some problems such as migration from iPhoto/Aperture to Photos which didn't always go as planned.

Keep in mind that I have almost always upgraded without doing any clean installs and I have noticed no problems. I do make clean install on my secondary Mac semi regularly because I use it for software testing.

If you have third party software that may complicate matters if they aren't compatible with newer OS.

 

[chrfr]

I wonder if the outcome would been better if I had make journey from Mavericks to Sierra with stops on every (or some) intermediate station(s). Anybody likes to share own opinion? Your input is welcome.

There's no need to install interim versions of the operating system when upgrading.

 

[Mac2013orlater]

There's no need to install interim versions of the operating system when upgrading.

However upgrade direct path is drawn by several stock apps user data issues - these are my own observations. Mail app got a mess of data, Safari dropped lot of user data generated prior to upgrade, similar with Finder.
reg. Mail - mail accounts not taken over properly
reg. Safari - browser history gone, Safari magic self-repair some days later
reg. Finder - list of visited Servers is gone
Basically no probs with 3rd party apps.