To upgrade on same hardware, generally in place migration sounds like a best option. However, I personally would not suggest in place migration. But I would suggest that you build complete new server.
Take last time full backups, detach the database files and keep it on other drive or server. Make sure you export the settings from MSDB and Master databases. (There are standard scripts from Microsoft which will help you export logins/users/jobs/ssis etc, you may google that).
Rebuild the machine with new OS and SQL Server. Restore the settings in Master and MSDB. Once you do that you have re-attach the database files to the server. Look for orphaned users and map them with logins, if any. Verify all ssis and jobs are set.
Swarndeep
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