UpdateSQL Error - 8.5 to 10.1.x

I have run the upgrade SQL on a copy of my 8.5 database 3 times now, and every time I get the following error. (Followed by a long list of other stuff that doesn't work.)

Starting applying schema patch [10.1-101888-AddCreatedDateUserIdToAllApplicationTables] at 2018-01-29 11:30:44

Msg 50000, Level 16, State 1, Line 98170

Failed to apply schema patch [10.1-101888-AddCreatedDateUserIdToAllApplicationTables], Error 515, Level 16, State 2, Batch Line 1: Cannot insert the value NULL into column 'CreatedUtcDate', table 'Infolink.dbo.cs_Wiki_Wikis'; column does not allow nulls. UPDATE fails.

If I close Management Studio, reopen it, and then rerun the upgrade script it will complete without errors. No other changes on my part. I am wondering if this is something that is known about? Is it something I should be concerned over? Is there something I should be doing that would avoid this error? 

I am a bit concerned because I have run the upgrade 3 times now. The first time, after getting past this error, everything looked pretty good for a couple of hours. Then the server just stopped responding. No visible errors. The browser wasn't getting a 50x error. Nothing. So I started over.

The second time things seemed to be better, after getting past this error. But after playing for a week I figured out something I had missed. My mistake. So overall not bad.

The third time I am not sure what went wrong. Something was messed up with JavaScript somewhere, because all of a sudden the button to get into the admin completely disappeared and there was nothing more to be done. 

So I am ready to give it another try, but thought I should ask about the SQL error first. Or possibly you have some idea what went wrong in the 1st and 3rd attempts? It is not giving me a lot of confidence.

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