There is no such thing as "an easy job" !

As always with AI, you'll have to validate and test this all.

Mostly no rocket science, but applied guidelines as they should.

It will get better over time ...

- outdated statistics?

- implicite conversions?

- functions in where clause?

- did you analyse the sqlplan using the free Solarwinds Plan Explorer ?

should be yourserver.yourdomain\yourinstance or yourserver.yourdomain,portnumber

Best is to file a bug for SSMS ( Help > Send Feedback > Report a Problem. )

Yes ( according to this MS art: Supported version and edition upgrades (SQL Server 2022) )

Here are some recommendations documented by MS with regards to your question: Database files and filegroups

Did you test having

ALTER DATABASE [YourDb] SET AUTO_UPDATE_STATISTICS_ASYNC ON

ref: Alter Database SET options

Be gentle with us 

#ChallengingRoadAhead

So ... nowadays still having win2003 OS with SQL2005 or worse comes into the picture 

Don't perform "in-place" upgrades!

You'll want to migrate to an new ( and supported ) OS anyway.

Request   2 OS : 1 temporary - 1 permanent target

• on the temporary, install SQL2014...

In SQLServer you cannot drop a PK when it is being reference by FK(s). It will produce an error.

That being said, as long as you don't change the data type...

Make sure all your consumers are also in the cloud ( to avoid traffic costs ! )

Check bundle prices / volume prices, maybe multiple SQLVMs come better than installing multiple...

Select ....
from msdb..sysjobhistory JH
inner join msdb..sysjobs J
on J.job_id = JH.job_id
Where J.enabled = 1 -- only active jobs
and JH.step_id = 0 
....

Keep in mind, you can launch disbled...

Keep in mind you can use DNS-aliasses instead of (client side) sql server aliasses !

If you rely on kerberos, you will have to register SPN(s) using the FQN of the...