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I recently inherited a SQL Server 2014 installation and I'd like to install updates. The virtual machine runs Windows Server 2016 standard.
I'm a developer and don't have much DBA knowledge.
Current plan is:
1) update 2014 to SP3 (right now its RTM) as 2014 went to extended support last summer
2) update to 2017/2019 in about a year
The server has about 50+ databases with 400Gb of data.
Is it a good plan? What kind of problems can I get? Will I need to back up all the data before major version upgrade? How much downtime can I expect?
I do plan to test it all on a separate machine with similar configuration, but I don't have access to Windows Server images and/or another VM to test it on, just my laptop.
One other thing - is there some script or utility to healthcheck the SQL Server installation? I doubt that manually running sql statements will be very thorough. I only found Brent Ozar's blitz so far

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    Yes, upgrade them to SP3 and the latest security update at least. sqlserverupdates.com It's best if you have test systems to test the upgrade first, but if not, you just have to do it. It will take 15 minutes or more, depending on your hardware. Get good backups first. SQL Server updates are extremely reliable. As far as future major upgrade plans--we can't really give good answer without knowing everything about the environment. Also, there are too many broad questions here that have no definite answer so this question will likely be closed. Please keep posts to 1 or 2 Qs. – Tony Hinkle 2 days ago