Is it possible to get OS X to remember my screen arrangement?
Even in 2019 macOS fails to preserve my monitor layout. I wrote a tool called displayplacer that lets describe your monitor layout as a terminal command. I then use BetterTouchTool to execute these profiles via hotkeys. It solved the same problem for me of using the same model monitor at work (in portrait mode) as at home (in landscape mode).

For example, on my 4 monitor setup at home I have this profile: displayplacer "id:A46D2F5E-487B-CC69-C588-ECFD519016E5 res:3840x2160 hz:60 color_depth:8 scaling:off origin:(0,0) degree:0" "id:F466F621-B5FA-04A0-0800-CFA6C258DECD res:1440x900 color_depth:4 scaling:on origin:(-1440,1437) degree:0" "id:4C405A05-8798-553B-3550-F93E7A7722BB res:1440x2560 color_depth:8 scaling:off origin:(3840,-363) degree:270" "id:18173D22-3EC6-E735-EEB4-B003BF681F30 res:1920x1200 color_depth:8 scaling:off origin:(960,-1200) degree:0"

Also available via Homebrew brew tap jakehilborn/jakehilborn &amp;&amp; brew install displayplacer